Vacation Home Rentals By Owner In Brewster, MA

A quiet summer home tucked off of 6A, adjacent to Nickerson State Park - great for hiking, biking, and swimming. Excellent location close to antiquing, shopping and golf, and 1.5 miles to Crosby Beach, with deeded rights to a private freshwater swimming pond (Owl Pond). Nice backyard, deck, fully equipped kitchen, 4 bedrooms, 2 full baths, and outside shower. Great for grandparents, parents and kids or 2 families! Air conditioning (window units) in each bedroom and in the living room, 3 cable TV's, and high speed Internet access and WiFi. brbrSheets, Bath Towels, Beach Towels, Beach Gear (chairs, umbrella, toys, etc.) are NOT provided. Guests must bring their own. Beds are 2 Queen and 4 Twin.

Great house for families - close to beaches, bike trail, dining!

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$553.22

Summary:brbrThe perfect pond getaway for families, boasting 3 bedrooms, a large back deck and new outdoor furniture to enjoy!brbrbrbrThe Space:brbrWelcome to Seymour Sunshine, a cheerful Cape Cod getaway on a Brewster backroad. Just a short stroll from the calm, clear waters of Seymour Pond, this inviting home offers the perfect blend of comfort, convenience, and charm for your next family vacation. With room for up to 8 guests, there is 3 bedrooms, and 2 full bathrooms. Seymour Sunshine is a bright and airy retreat ideal for beach days, pond paddles, and slow summer mornings on the deck.brbrbrbrStep inside and you’ll find a beautifully updated kitchen with sleek stainless steel appliances and plenty of space for whipping up fresh local meals. The open-concept layout flows into a cozy dining area and living room, perfect for board games, or relaxing with a book after a day in the sun. For those mixing work with vacation, a dedicated work-from-home station ensures you can log in with ease—then log off and hit the water just as quickly.brbrbrbrSliding doors lead to a spacious back deck, newly furnished with comfortable lounge seating and an outdoor dining table. Fire up the grill for a sunset cookout, unwind under the stars, or sip your morning coffee while the birds chirp from the surrounding trees. Downstairs, the finished basement provides even more room to spread out—great for game nights as you play with the Foosball table or the Air Hockey table.brbrbrbrAfter a refreshing swim in Seymour Pond head out to explore Brewster’s many charms. From scenic trails at Nickerson State Park to shopping and dining at Lemon Tree Village, everything you need is close by. Stop in for casual bites at local favorites like Cobie’s or Kate’s, or indulge in a sunset dinner at Chillingsworth or Spinnaker.brbrbrbrWhether you’re planning beach days, bike rides, or just soaking up the Cape air with the people you love most, Seymour Sunshine is your perfect home base for a relaxing, sun-drenched stay in Brewster just 0.5 miles away from the Cape Cod Rail Trail and 1 mile from Long Pond Brewster Public Beach.brbrbrbrbrbrLayout of Bedrooms & Bathrooms: brbrbrbrMain LevelbrbrBedroom #1 - King BedbrbrbrbrBathroom #1 - First floor, shower. Includes washer/dryerbrbrbrbrUpper Level brbrBedroom #2 - Queen BedbrbrBedroom #3 - Queen and DoublebrbrbrbrBathroom #2 - Second floor, tub + showerbrbrbrbr**Linens and bath towels are included.**brbrbrbrOther Things to Note:brbr-

Walk to Seymour Pond beach

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$729.25

Brewster GetawaybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your private retreat in Brewster, MA, nestled in the charming Highlands Neighborhood. This delightful house combines modern comfort with a touch of New England charm, making it the perfect getaway for families and friends alike. With deeded rights to Seymour Pond and easy access to the Rail Trail (2 adult and 2 children's bicycles and helmets provided) just five minutes away, outdoor enthusiasts will find themselves in paradise. The beautiful Bay Beaches are less than threemiles from your doorstep, offering sun-soaked days by the water. Or, visit Punkhorn Conservation Land just a short drive away.brbrThe home features a private yard complete with an outdoor shower, perfect for rinsing off after a day at the beach. Enjoy al fresco dining on the deck or patio, equipped with comfortable furniture and a gas grill for those summer barbecues. Inside, you'll find all the amenities you need for a relaxing stay, including a fully equipped kitchen, WiFi, and a cozy living room with cable TV and board games for family fun.brbrBrewster is a treasure trove of galleries, farms, restaurants and shops, ensuring you’ll never run out of things to explore. For golf enthusiasts, Captains Golf Course and Cranberry Valley Golf Course are nearby, while Nickerson State Park offers stunning trails and natural beauty. brbrWhether you're seeking adventure or relaxation, this Brewster home is your gateway to the best of Cape Cod. Book your stay today and create unforgettable memories in this idyllic setting!brbrThings To Knowbrbr-Close to Bayside Beaches (under 3 miles)br-Close to the Rail Trailbr-Bicycles providedbr-Close to golfbrbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Cape Cod Getaway - near Seymour Pond and Rail Trail; Bay Beaches w/in a few mile

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$778.26

***ONLY 1 SUMMER WEEK LEFT~6/26-7/3*** brThis is a wonderful week to be on the Cape! The days are the longer, the beaches are quieter, and it is pretty easy to get a reservation at your favorite restaurant!brbr*Recent exterior and interior renovations include:br-beautiful, large, custom outdoor showerbr-deck with cable rail system br-bluestone patio w/ fire pit, large driveway, and walkwaysbr-forced hot air/AC system for the first floor(our house has full AC w/2nd floor master bedroom split)br-siding, trim, sliding doors, and windowsbr-first floor including kitchen, two bathrooms, three bedrooms, all painted and updatedbr*Hardwood floors throughoutbr*Tranquil, private setting close to everything Cape! Brewster is 31 miles from the canal and 31 miles to Provincetown...the ideal location!br*Fast, dependable WIFIbr*3 Smart TV’s with YouTube TV provided br*Please bring your own sheets and bath towels OR optional linen/bath towel service available upon request. Price $140. br*Kayak rentals available upon request for a small fee.brFRESH WATER OR SALT WATER brYou can have BOTH! Book your vacation at this modern yet cozy, fresh water, pond retreat in the heart of BREWSTER, nestled in the woods, surrounded by songbirds. Our home is very close to bayside and Nantucket Sound beaches, and a short drive to Cape Cod National Seashore!brbrSip your morning coffee or tea out on the private dock observing the resident ducks and swans as the sun rises over the water. Rent our kayaks or bring your own paddle boards, kayaks or canoes and explore on this pristine, 93 acre kettle pond which directly connects to even larger Upper Mill Pond. Observe the full moon over the water from the dock, deck or 2nd floor master suite~gorgeous!brbrShare barbecue, boiled lobster, or takeout on the deck, and enjoy an evening campfire overlooking the pond. Inside is ample space for end-of-the-day home entertainment - music, TV, or movies. In case of a rainy day, there are games, puzzles, ping pong, Foosball, mini-pool or settle in with a great book!brbr4 bedrooms (ALL air conditioned and with ceiling fans)sleep 8 comfortably on king, queen, full and twin beds. brbrThere are 3 FULL BATHROOMS including one off the main hallway with a tub/shower. The first floor queen bedroom has a connecting private bathroom with pedestal sink and walk- in marble tiled shower. The second floor master suite has its own marble tiled bathroom with double sinks and a walk-in shower.brbrThe kitchen boasts quartzite countertops, tile backsplash, all stainless steel appliances, a large island with seating for 4, farm table with seating for 7, hardwood flooring and beautiful, large windows and slider overlooking the pond! brbrYou will find laundry machines in the clean, unfinished basement down one level, along with a workout space, full sized ping pong table, foosball table, mini-pool table, and extra Adirondack chairs for outside relaxing. Walk out from basement through French doors onto a short pathway to our private dock and custom outdoor shower.brbrThis is the perfect property for those wanting a beautiful, updated, clean, open concept home on the water. It is centrally located and close to everything! brOur home is available June - August.

Renovated, Spotless, Pond Front w/ Kayaks ~ Minutes to Brewster & Dennis Beaches

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$370.26

The Blue Whale CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrBrewster Bay Beaches Retreat | Explore Orleans, Chatham & ProvincetownbrWelcome to your newly renovated Brewster Cape Cod retreat. This one-level private home is ideally located near Nickerson State Park, the Cape Cod Rail Trail, The Captains Golf Course, and the iconic Brewster Flats — and is central to Orleans, Chatham, Provincetown, Dennis, and Hyannis/Harwich for ferry access to Nantucket and Martha’s Vineyard.brbrSet in one of the Cape’s most charming towns — known for historic captain’s homes, classic inns, exceptional dining, calm bay beaches, and relaxed summer evenings — this home lets you explore by day and return to your own private haven at night.brbrDesigned for easy summer living, this bright 3-bedroom, 2-bath ranch features an open floor plan that keeps everyone connected. The fully accessorized kitchen makes beach mornings and family dinners effortless, while hardwood floors and updated bathrooms add modern comfort. The inviting living room offers space to unwind, and all bedrooms include window AC units and TVs. The primary suite features a spacious luxury shower. A washer and dryer are available for your convenience.brbrThe light-filled sunroom is perfect for morning coffee, board games, or winding down after a day at the bay, biking the Rail Trail, or barbecuing in the backyard.brbrLocated in a walkable Brewster neighborhood, the home offers a rare combination of privacy and the ability to enjoy peaceful morning or evening strolls right outside your door.brbrSpend your days discovering Cape Cod and the Islands — then return each evening to your private Brewster retreat, where comfort, location, and neighborhood charm come together.brbrThings to KnowbrCheck-in time: 4:00 PM.brCheck-out time: 10:00 AM.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.brStreaming services available with guests’ own account(s).brGuests must bring their own firewood.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. No more dogs are allowed.brParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Newly renovated ranch with a private yard & central location

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$586.25

Elegant Coastal CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrJust a short drive from multiple beaches, this quiet and spacious Brewster home has it all! Some of your favorite memories will be made outside, in the expansive outdoor space, equipped with a large patio, grill, and yard games. This space is the perfect location for sunset grilling sessions and evening cocktail cheers. Adult bikes are also available for when you'd prefer to explore the neighborhood. Extend the opportunities for amusement by visiting the nearby Dennis Pines Golf Course, the Cape Cod Museum of Natural History, Stony Brook Grist Mill, and Crowes Pasture Conservation Area. brbrBack at your home away from home, settle down in front of the living room's large smart TV or engage in some playful competition over a board game. With DVDs and streaming capabilities available, you'll never run out of things to watch! Follow the home's elegant decorations into the fully equipped kitchen, displaying granite countertops and stainless steel appliances. brbrThis home features two 'main bedrooms':brBedroom 1: Located on the 1st floor, this room includes a king bed and a full en suite bathroom. The clothes washer and dryer are conveniently located here.brBedroom 2: Situated on the 2nd floor, this bedroom also offers a king bed and a full en suite bathroom.brBedroom 3: Found on the 2nd floor, this room is furnished with a queen bed.brBedroom 4: Also on the 2nd floor, this bedroom provides two twin beds.brbrThere is an additional full bathroom on the 2nd floor and a half bath, known as a 'powder room,' located off the living room on the 1st floor.brbrMoreover, the house is equipped with a total of four TVs:br50” smart TV with Firestick and DVD player in the living roombr48” smart TV in the three-season roombr40” TV with Firestick in the 1st-floor master bedroombr40” TV with Firestick in the 2nd-floor master bedroombrbrAs you explore the rest of the home, you will find four inviting bedrooms, all adorned with soft linens, central air, and ample storage space. Additional features you'll love about the home include its gas fireplace, private washer/dryer, and central air-conditioning. brbrThings to KnowbrbrParking notes: There is free parking available for 6 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Ideally located home with yard, grill, bikes, gas fireplace, streaming, W/D, AC

Brewster, Massachusetts, United States

4

Bed

Bath

8

Sleeps

$466.11

Your Next Beach Getaway!brbrEscape to this stunning, newly renovated 2-bedroom townhome located in the luxurious Ocean Edge Resort, nestled on a picturesque golf course. With an array of incredible amenities at your fingertips, this serene retreat is the perfect destination for your Cape Cod vacation. Conveniently, a 5 minute walk to the gym, an indoor pool, an outdoor pool, pickleball and tennis courts! 5 minute drive to the Linnell Landing beach & 20 minute drive to Nauset Beach!brbrThe Space:brbr- A queen bed in the primary bedroom,br- Two twin XL beds in the second bedroom,br- A cozy pull-out queen sofa in the living room for additional guests.brbrThe home features 1.5 fully stocked bathrooms (complete with soap, towels, and a hair dryer), with one conveniently situated near the washer and dryer. Step out back to your private oasis, where you’ll find views of the forest, a fire pit for cozy evenings, and a grill perfect for summer BBQs.brbrThe kitchen is brand-new and equipped with stainless steel appliances, a wine fridge, and everything you need for your stay, including cookware, utensils, and dishware. It’s fully functional and ready for anything from quick meals to full dinners.brbrOcean Edge Resort Named Cape Cod's Best Hotel in 2023 by Boston Magazine!brbrOcean Edge offers exclusive amenities for guests to enjoy:brbr- 5 sparkling pools (2 indoor, 3 outdoor), including the Fletcher Pool with a sauna Arbor pool with a snack bar and fully stocked bar,br- Private beach fires and activities on the mansion’s front lawn (like cornhole),br- Pickleball and tennis courts,br- Kayak, paddleboard, and bike rentals (ideal for exploring the nearby Cape Cod Rail Trail),br- A full-service spa and three fitness centers,br- Two mansion restaurants: one indoors and one offering breathtaking bayside views.brbrActivities & Pricing:brAs a sponsored guest, you’ll have access to all of these incredible amenities for a small additional fee.brbrGuest Passes (Pools, Fitness, and Activities):brbrDaily: Adults $25 | Children $10brWeekly: Adults $75 | Children $30brbrbrFitness Classes:brSports Club Classes: $25 per classbrYoga on the Beach: $15 per sessionbrbrBike Rentals (First-Come, First-Serve):brHalf-Day: Adults $22 | Children $18 | Toddler Trailer $15brFull-Day: Adults $35 | Children $25 | Toddler Trailer $15brbrBlueberry Pond SUP & Kayak Rentals (Per Hour):brSingle Kayak: $24brStand-Up Paddleboard: $22brbrWhether you’re lounging by the pool, playing a game of pickleball, kayaking through Blueberry Pond, or relaxing by the fire pit with a drink from the bar on the beach at Ocean Edge, this fabulous townhome and resort have everything you need for an elevated, classic Cape Cod vacation.

Newly Renovated 2-bedroom townhome 5 minutes from the beach!

Brewster, Massachusetts, United States

2

Bed

1

Bath

6

Sleeps

$10291.99

This expansive contemporary 5BR/6BA home is the perfect vacation home- stylishly and impeccably furnished with quality throughout every aspect of this home. brbrThe main floor boasts an open, state of the art, granite stainless kitchen that will make it hard to leave at the end of the week!! The kitchen is spacious, open and fully stocked with everything you may need. Overlooking the dining area with seating for eight, to a comfy, but spacious living room with large HD TV. Each bedroom is well appointed with resort suite quality finishes and touches. The area above the garage offers additional guest quarters and a full bath. There is electric car charging available, but please bring a cord. You can enjoy cookouts on the patio with stunning grounds and in the evening take in the breathtaking sunsets over Cape Cod Bay. brbrMants Landing Beach (Cape Cod Bay) offers warm, calm water when the tide is high to take advantage of activities including fishing, swimming and kayaking. Take a walk on the flats at low tide-you can venture out over a mile-to gather hermit crabs, clams, shells and sand dollars among other treasures. This is a spectacular location for your family to relax and enjoy your Cape Cod vacation. brbrNon-refundable $500 Administrative fee, Cleaning fee $780 (Linens Included), plus applicable state and local taxes.

Impeccable 5BR Custom Home - Short stroll to Mant's Landing Beach

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$1277.36

Enjoy the best that Cape Cod has to offer! Located in a private association neighborhood with tennis, pickleball & bocce courts and direct access to the Cape Cod Rail Trail, just 3 doors away!. Drive or bike to Crosby and Skaket beaches on the Bay Side or plan an over the sand drive onto Nauset Beach. Experience Cape Cod's other sand at several challenging golf courses within a 15 minute drive. At the end of each day, take a refreshing swim in the salt water pool, relax with a cocktail at the edge of the koi pond, or roast marshmallows at the fire pit. brThis house is newly furnished!!!brBEDS & BATHSbrThere are sleeping accommodations for 8 people in 4 bedrooms. brThe main upstairs bedroom boasts a king bed with a remote. brThe second upstairs bedroom has 2 twin beds. brThe upstairs bathroom has two sinks, a toilet and a large tiled walk in shower with an adjustable water wand and a rainfall shower head. brThe two downstairs bedrooms each have queen beds. brThe downstairs bathroom has a sink, a toilet and a large tiled walk in shower.brAll of the beds and furnishings are new! brLinens and towels included.brKITCHENSbrYou'll find that the kitchen is fully equipped for almost any occasion.brBoth indoor and outdoor countertops are granite with stainless sinks. brThe main kitchen has all stainless appliances. This includes a dual oven, electric stovetop, microwave, large refrigerator/freezer, dishwasher, toaster oven, Kurig coffee maker, electric hot water kettle, blenders, mixers and (of course) a lobster steamer!!brThe outdoor kitchen has a sink, Weber Genesis propane grill and wine/beverage fridge. brDININGbrThere are indoor and outdoor dining options with large tables each with seating for 8.brThe breakfast bar has three stools.brLIVNINGbrPlenty of space to stretch out inside!brThe living room is furnished with a brand new sofa, comfy chairs with ottomans and a 55 Smart TV. Gas fireplace has a remote control to regulate the temperature.brA second cozy living area is in the finished basement with a large sectional, chairs, a 65 Smart TV and a bar with 4 stools. There are several games, such as Pictionary and Trivial Pursuit, as well as cards and poker chips for game nights.brThere is a couch and ping pong table in the garage.brOUTDOORSbrThe entire backyard is surrounded by a privacy fence. brOutdoor kitchen and dining area are on the elevated flagstone patio looking over the backyard amenities.brSectional seating for 8 people is located in the patio area next to the koi pond.brCross the bridge over the koi pond to our fire pit area.brAll of this is within steps from the saltwater pool lounge area. brThe outdoor shower has both exterior access and direct access to the first floor bedroom.brPARKINGbrThe private driveway can accommodate 4 vehicles. brThere is no on street parking and the garage is for storage and ping pong only.brbrOTHER STUFF YOU SHOULD KNOWbrbrThe home is cooled by separately controlled minisplits. Heat is gas-fired forced hot water for the entire house. The gas fireplace in the living room can also be used for makeup heat.brLaundry room has a washer and dryer for your use.brWe provide fresh linens and bath towels.brThere is an information binder on the house operation, beach access and recommendations on local restaurants and activities. brAlso for your use;br4 bicyclesbr8 beach chairsbr2 beach umbrellasbrBeach cartbrFor safety, because of the pool, please keep the glassware inside. We have non-shatter beverageware for outdoor use. brPlease be courteous to our neighbors and keep the noise levels down, especially after 10 pm.brMinimum stay is for 7 nights, Sunday to Sunday. If feasible, we may accommodate a different start day.

Private Vacation Oasis with Pool, Outdoor Kitchen & Koi Pond!

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

Select Dates for Price

Northside Retreat: 5-Bedroom Vacation Haven with Endless Outdoor FunbrbrWelcome to your perfect Cape Cod getaway! This stunning 5-bedroom vacation home is located on a sprawling lot on the Brewster-Dennis line, offering endless opportunities for relaxation and recreation. The private heated inground pool is the centerpiece of the outdoor space, surrounded by multiple areas for dining, lounging, and playing games, making it ideal for creating unforgettable memories with family and friends.brbrInside, the open-concept kitchen, dining, and living area is perfect for gathering together, while additional spaces, including a second living room, provide plenty of room to spread out and unwind.brbrLocated just a mile from Sea Street Beach on Cape Cod Bay, the home offers easy access to some of the best beaches on the Northside. The location is truly supreme—situated near Route 6A, you’ll be close to the Cape’s finest restaurants, charming shops, and unique antique stores, offering something for everyone.brbrWhether you're relaxing poolside, exploring the nearby beaches, or discovering the charm of Cape Cod’s historic Northside, this home is your gateway to a perfect vacation. Don’t miss out on this incredible retreat!

5-Bedroom Vacation Haven with Pool!

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$585.73

Relaxing Cape GetawaybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis charming Cape Cod getaway is just 15 minutes from Chatham and packed with inviting features including dramatic vaulted ceilings with skylights, a spiral staircase, and a spacious back patio complete with a gas grill—perfect for relaxed outdoor dining. The airy first-floor living area welcomes you with comfortable sofas and chairs, bathed in natural light from a sliding glass door that opens to your private patio. The full kitchen offers ample cabinetry, plenty of counter space, and all the equipment needed for home-cooked meals. Enjoy gathering around the dining table, which seats six indoors or enjoy alfresco meals on the patio with room for four, while the kids play on the lawn.brbrThe flexible sleeping arrangements include a first-floor bedroom with a double bed and sofa, plus a full bath with a shower/tub combo. Upstairs, a cozy loft features a king-size bed, an en suite bath, and a large sofa—ideal for unwinding or finding a little extra privacy.brbrDuring your stay, take advantage of the exceptional amenities available at Ocean Edge. Guests have the option to purchase resort passes for access to five sparkling outdoor pools, indoor and outdoor hot tubs, a modern fitness center, tennis and pickleball courts, and fun family activities. There are convenient on-site rentals for bikes, kayaks, and stand-up paddleboards, with scenic paths, nearby Blueberry Pond for paddling, and a shipwreck-themed playground sure to be a hit with kids. Seasonal and year-round pools, plus great options for dining, mean you’ll have everything you need close at hand.brbrWhen you’re ready to explore further, hike scenic trails at Sheep Pond Woodlands, bike along the famous Cape Cod Rail Trail, or discover the shops and restaurants in historic Chatham. This welcoming retreat is your perfect home base for a classic Cape escape, relaxing days and family adventures included!brbr2026 Ocean Edge Guest Pass Information:br• Amenities available with guest pass (fees apply):br – Pool access: $32/day or $96/week adult, $16/$48 childbr – Fitness center: Free with pass; classes $25br – Tennis/Pickleball: $24/hr per courtbr – Bike rentals: $25–$35 adult, $20–$30 childbr – Kayak/SUP (Blueberry Pond): $30–$40/hr kayak; $35/hr SUPbr• Kids’ activities and shuttle included with passbr• Passes must be picked up and paid by credit card at the Linx Clubhouse (832 Villages Dr)br• Amenities, rates, and hours subject to changebr• A shuttle is required to access Mansion diningbrbrThings to KnowbrGuest passes are required and must be kept with you at all times as your identification & access keybrGuests do not have access to the Ocean Edge Private Beach or Bayside Pool.brAmenities are available to registered guests only. Fees, amenities, and hours are subject to change. brCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by Vacasa’s good neighbor policy and shall not engage in illegal activity. brQuiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brProperty tax ID: C0036100410brbrParking notes: There is free parking available for 1 vehicle.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Lovely home w/free WiFi/spacious patio/spiral staircase - near shops/restaurants

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$761.95

Sheep Pond Bow HousebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled in the serene South Hill neighborhood of Brewster, MA, this charming reproduction of a classic Cape Cod Bow House offers the perfect retreat for families seeking tranquility and outdoor adventure. Just a short walk down a sandy dirt road leads you to the private beach on Sheep Pond, a peaceful oasis where motor boats are not allowed, ensuring a quiet atmosphere ideal for kayaking, swimming, and relaxing by the water.brbrThis dog-friendly home is thoughtfully equipped with amenities to enhance your stay, including two kayaks, sand toys for the kids, and a selection of board games for family fun. The cozy interior features a washer/dryer, AC, and a kitchen with modern appliances, making it easy to prepare meals after a day of exploration. Enjoy your evenings on the spacious deck, complete with comfortable furniture and a gas grill for outdoor dining.brbrThe property also boasts a small frog pond, adding to the charm of the lush surroundings. With easy access to local attractions such as beaches, restaurants, and scenic drives, this vacation rental is perfect for those looking to immerse themselves in the natural beauty of Cape Cod. Whether you're fishing, bird watching, or simply soaking in the peaceful ambiance, this home is your gateway to a memorable getaway. Book your stay today and experience the best of Brewster!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brThere is a frog pond onsite, small children MUST be supervised at all times in the yard.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Cozy family retreat with kayaks, board games, AC, and beach access

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$373.5

Paradise by the BaybrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrVacationers, take notice of this perfect Brewster home, perfect for getaways any time of year! The summer months are some of the best imaginable here. Spend your days at the private community beach, then return home for a relaxing outdoor shower to wash the sand and salt away before sitting down for dinner on the stunning back patio. This home also features a full kitchen and a dining table with seating for ten.brbrWith a design that exudes comfort, coziness, and a homey charm, every corner of this retreat has been thoughtfully arranged to enhance your overall experience.brbrWHAT’S NEARBYbrJust a few hundred feet down Nelson Street there is a large, private community beach for owners and guests of homes in the neighborhood. The Ocean Edge Resort, golf course, and restaurant is less than a quarter-mile down Route 6A, as well as Main Street Brewster which hosts supermarkets, gas stations, and retail stores of all types. brbrTHINGS TO KNOWbrbrParking notes: There is free parking available for 5 vehicles.brbrSecurity camera details: There is an active front door security camera at this home.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Secluded ranch home with a full outdoor shower & private community beach

Brewster, Massachusetts, United States

Bed

2

Bath

7

Sleeps

$485.27

Unwind in Brewster at this updated house perfect for families or groups. With five bedrooms featuring three king beds (one can be two twins), two queen beds, and three living room areas, guests find plenty of space to relax. 3.5 bathrooms include both bathtubs and showers, making getting ready easy. Office space if you need to get some work done. Well equipped large kitchen. Perfect for meals with family and friends. Dinning area can seat up to 12 people. Wellness room includes sauna, salt room, and exercise equiptment. Games for added fun. Enjoy all that Cape Cod has to offer when you stay at our place. New listing here, but a guest favorite on other booking site.

Spacious & Updated Rare Cape Cod Find. Wellness room.

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$872.88

AVAILABLE AS AN OFF SEASON RENTAL AS WELL FOR 3 NIGHT MINIMUM RENTALS! brLocated just .4 Miles from Paine's Creek Beach this 4 Bed / 3 Bath home sleeps 8 comfortably. Featuring a crisp modern design and layout, you and your guests will relax and enjoy sparkling water views over Freemans Pond. Wall mounted AC units will ensure you stay comfortable on those balmy summer nights, and an enclosed outdoor shower awaits for you to rinse off after a day at the beach. At night, grill up some food on the gas grill and watch the light fade over the water. Don't miss out on your chance to reserve your space at this wonderful home. brTenants provide their own linens and towels. No pets, please. Saturday to Saturday, 7 night minimum rentals during the peak season. Subject to applicable taxes and fees. All Robert Paul Vacation Rental bookings include a non-refundable $250 fee that includes administrative fee and damage waiver assurance for self-reported incidental damage up to $1,000.00. Upon receipt of a booking request, an agent will reach out to discuss additional security protection which may be required at this property.

Stunning Waterfront Brewster Rental Close to Beach RPAM019

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$586.6

Cozy Charming CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrMake the most of your Cape escape at this home. Situated on a friendly, quiet street in the charming town of Brewster, this rental is a short walk from a deeded beach on Seymour Pond and the Cape Cod Rail Trail.brbrInside, lots of windows and vaulted ceilings provide ample natural light, while brand-new furnishings make it easy to relax. The main living area features soaring vaulted ceilings and handsome wooden beams. New furnishings include a sofa and a love seat. Stream Netflix shows or select one of the 205 channels provided with the cable package. The 60” smart TV in the second living area allows access to streaming services as well as channels playing NFL, NBA, and MLS games. Cozy up on the sectional, peruse one of the Cape Cod guidebooks available in the house or play a board game around the table. Stainless steel appliances sparkle in the convenient full kitchen. Prepare tasty meals on the island. Handy extras include a waffle iron, George Foreman grill, and popcorn maker. When you’re ready to eat, you have your choice of four different dining areas in the house or on the deck.brbrRelax on the brand-new deck, furnished with a sofa and a coffee table. Prepare meals on the gas grill and dine at the table. Find ample space to play in the grassy backyard -- complete with a hammock and gas fire pit with surrounding seating. There is also a large bluestone patio in the backyard.brbrOther perks include an A/C unit in each bedroom, two wall-mounted 60' TVs, a firepit, and a 600mbps Wi-Fi network.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brThe fireplace is not operational.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$427.79

Cape Landing CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLocated on a quiet dead-end street, this 2,150 square foot home is just 175 yards from Linnell Landing Beach on Cape Cod Bay! Bike the Cape Cod Rail Trail -- you can hop on at Deer Road, just half a mile from your rental. Explore the trails and kettle ponds of Nickerson State Park, also within walking distance. You’ll find plenty of shopping and dining options in walkable Brewster.brbrInside, the spacious living area is appointed with a smart TV for comfortable lounging. Plan the day’s adventures in the office, outfitted with a writing desk and printer. For something more mellow, grab one of the many books in the home and catch up on some reading. Prepare tasty meals in the roomy, full kitchen, featuring a full suite of appliances as the kids frolic in the large yard.brbrFire up the gas grill and dine alfresco on the main patio, or relax in the Adirondack rockers on the side patio as you gaze out towards the water. Your retreat also includes a convenient outdoor shower for washing off that loose beach sand.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brNo steps are required to access this two-story home; however the stairs to the second-floor bedrooms are narrow and steep.brThe fireplaces in the living room and office are not operational.brbrParking notes: There is free parking available for 4 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Classic Cape Cod beauty with patio, grill, & office - minutes to beach

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$440.72

Relax with your family in a roomy, clean and quiet setting. Nestled on a private road, this home is less than a tenth of a mile to Grandfather's Beach. Families have easy access to swimming, exploring tidal flats, hiking and the Cape Cod Bike Trail. Conveniently located near bike rentals, shopping and a variety of restaurants. This is the perfect location to explore Brewster's many antique shops and quaint local landmarks, or just a short drive to more commercial summer attractions. After a busy day, one can enjoy dinner on the deck, then walk to the beach for spectacular sunset views! Available for 3 Night Minimum Stays (during the off season ONLY).brbrNon-refundable $325 Administrative Fee, Cleaning Fee $250, plus applicable state and local taxes.

Spacious home less than .1 mile to private assoc beach

Brewster, Massachusetts, United States

Bed

Bath

Sleeps

$680.98

NEW RENTAL LISTING IN 2025: Discover the beauty of Brewster from this charming 3-bedroom house with private pond access at the end of a cul-de-sac. With 3 queen beds and 1 twin bed, this adorable property offers a cozy retreat for guests. The 4 bathrooms feature 3 showers and 1 bathtub. Enjoy the convenience of amenities like window AC units, washer/dryer, cable TV and WiFi. Open floor plan on the main floor with large family room, kitchen with counter seating and den with couch and full size eat in dining space. Three sliding doors to the deck facing the pond gives the home an airy feeling and provides a perfect way to enjoy indoor and outdoor space. The large pond-facing deck has a covered and screened in section attached to the primary bedroom. The deck also has a full size dining table and gas grill perfect for morning coffee, family dinners and evening smores. Kayak and fish from the private pond access. brThis house is centrally located and a safe bike ride or walk to the following- brbrBrewster Village Market: 0.6 milesbrBrewster General Store: 0.9 milesbrLemon Tree Village Shops: 1.5 milesbrCape Cod Rail Trail access: 1.9 milesbrPaines Creek Beach: 2 milesbrbrOther area attractions:brCape Cod Bay beaches and local pond beaches- 10 min drivebrBrewster Whitecaps home field- 10 min drive

Charming 3-bedroom pondfront house on cul de sac in Brewster, Mass NEW LISTING

Brewster, Massachusetts, United States

Bed