Home Vacation Rentals By Owner In Brewster, MA

Showing 331 Of 331 Vacation Rentals
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Exceptional(51)

$586.6

/ Nightly
Private Vacation Home

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

Brewster, Massachusetts, United States

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.
Bed 3

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Bath 2

Bath

Sleep 9

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Exceptional(33)

$427.79

/ Nightly
Private Vacation Home

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

Brewster, Massachusetts, United States

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.
Bed 4

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Bath 2

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Sleep 8

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$640.11

/ Nightly
Condo

This Beautiful Bayside is located in Fieldstone, with central AC (minus in the small bedroom).

Brewster, Massachusetts, United States

Two-Story Townhouse in Ocean Edge with Peaceful Pond Viewsbrbr* * * * See end of this description for information about free included activities and our cancellation/refund policy * * * *brbrEnjoy tranquil pond views and modern comforts in this inviting Ocean Edge townhouse. Updated with a renovated kitchen and central A/C throughout most of the home (note: the small third bedroom has a floor fan only), this property is designed for easy, relaxing Cape Cod living.brbrThe first floor features a fully equipped kitchen with new countertops and cabinetry, opening to a comfortably furnished living room with a mounted flat-screen TV (NESN and Golf Channel included). Sliding glass doors lead to a spacious, furnished deck complete with a gas grill—perfect for outdoor dining. Also on this level is a bedroom with a full-size bed and twin bed, conveniently located next to a full hallway bath.brbrUpstairs, the primary bedroom offers a plush king-size bed, TV, en-suite bath, and private deck overlooking the serene pond. A third bedroom includes a twin bed and a trundle bed, ideal for additional guests.brbrA covered garage is available for owner storage.brbrCANCELLATIONS, CHANGES & REFUNDS brIn the event of cancellation, a refund minus a service fee of 25% of the total rent rate will be made if and ONLY if rental property is re-rented. The $205 booking & damage protection fee is non-refundable. If rental property is not re-rented, cancellation will result in the forfeiture of the total rental amount paid. All notices of cancellation must be in writing.brbrFREE ACTIVITIESbrYour stay includes up to $597 per week in complimentary activities (subject to season and valid for stays up to 27 nights or less). By booking with us, you'll receive free tickets—every day of your stay—to top activities, including:br-Golfingbr-Bike & Kayak Rentalsbr-Whale Watcher Cruisebr-Round Trip Ticket to explore Martha Vineyard & NantucketbrbrNote: Saturday-to-Saturday stays only.brbrSponsored Guest Pool Passes:brbrGuests may purchase Sponsored Guest Pool Passes, which include access to Arbor and Fletcher Pools, the Fletcher Cardio Center, and scheduled children's activities throughout the Villages.brTennis and pickleball courts are also available for use. (additional fee may apply)brbrPool passes are NOT included in your stay and must be purchased separately. The Ocean Edge Resort Golf Club manages the distribution, fees, and operations of all amenities, which are subject to change without notice.brbrAdditional Information:br-Smoking is not permitted.br-Pets are not allowed.br-Bed sheets, pillowcases, and towels are provided. (Beds Made!)br-Travel Insurance is available upon request.br-Payment accepted via Visa, Mastercard, American Express, & e-Check. brbrLeighton Rentals - BP0397
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(2)

$680.98

/ Nightly
Private Vacation Home

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

Brewster, Massachusetts, United States

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
Bed 3

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Bath 3

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Sleep 7

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$1514.68

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Private Vacation Home

3BD Beach Dunes Beachfront Lighthouse--A/C, Deck, Direct Water Access, Amazing Water Views & Sunsets

Brewster, Massachusetts, United States

Beachfront lighthouse at Brewster Dunes! Amazing Cape Cod Bay water views from the deck, balcony and top of lighthouse! Direct water access!brbr* * * * See end of this description for information about included FREE ACTIVITIES through Xplorie, the Kinlin Grover Compass CANCELLATION/REFUND policy and more! * * * * brbrYou may never want to leave this charming Cape Cod escape with inviting interior and wonderful outdoor spaces.brbrThis lovely three-bedroom home is part of a private community with 450 feet of private, shared beach. Enter an open main living area with kitchen, living room and dining area. The living room has comfortable seating and a flat screen TV with cable. The nicely equipped kitchen has stainless appliances. A slider from the living room leads to the covered deck. There is a bathroom with a shower on this floor. brbrSteps lead to the second floor with three bedrooms and a bathroom with two sinks and a tub/shower. The primary bedroom has a king bed and balcony with gorgeous views of the water. brbrThe second bedroom has a queen bed and the third has a full (double) bed and a twin bed.brbrFollow the steps from the second floor to the third floor lighthouse where the panoramic views of Cape Cod Bay are breathtaking! Wonderful spot for star gazing, sunsets, birdwatching and quiet contemplation.brbrCentral air conditioning, washer/dryer, cable and WiFi. brbrThe covered deck has a dining table, lounge chairs and gas grill. Enclosed outdoor shower at the front of the house. Follow the path--less than 100 feet from the house to the private, shared beach for swimming, kayaking, sunbathing and beachcombing. Explore Brewster's beautiful flats at low tide.brbrWalk or bike to 6A for a lobster roll at JT's or breakfast at the Kitchen Cafe. Pick up a bestseller at the beloved Brewster Bookstore to read on the deck on the lighthouse. Close to amazing Brewster restaurants, coffee shops, stores and galleries. Short drive to Nickerson State Park, the Crosby Mansion and the Cape Cod Museum of Natural History. Bike along 6A and pick up the Cape Cod Rail Trail bike path.brbr* Additional fees br- $220 non-refundable reservation fee; $30 damage protection fee (no security deposit required); guest services feebr- all applicable taxesbr* FREE WIFIbr* SATURDAY TO SATURDAY RENTALbr* NO PETS (no exceptions)br* NO SMOKINGbr* OCCUPANCY: 6 (adults and children)br* PARKING FOR 2 VEHICLESbr* Sheets and towels providedbrbr**** FREE ACTIVITIES INCLUDED ****brTo enhance your vacation experience, Kinlin Grover Compass includes Xplorie, which means free admissions and equipment rentals everyday of your stay at select popular attractions in the area. brbrAs a guest of Kinlin Grover Compass, you'll receive free tee-times, free equipment rentals, free admission and free tickets to some of Cape Cod's best activities! Activities and availability are subject to change. Not available on stays over 28 days.brbr**** CANCELLATION/REFUND POLICY ****brUpon cancellation for ANY reason, money will be refunded less a 20% service fee of the total rental amount due, ONLY if the property is re-rented for the same terms and conditions of the original Agreement. Tenant further acknowledges and agrees that where Kinlin Grover Compass undertakes to re-let the property, the rental fee to be charged to the substitute tenant shall be in an amount to be determined in the reasonable discretion of Kinlin Grover Compass and Owner. Tenant agrees that any cancellation of the reservation, undertaken at any time, shall not be effective unless in writing and delivered to Kinlin Grover Compass.brbrKGC BNEED
Bed 3

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Bath 2

Bath

Sleep 6

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$778.19

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Private Vacation Home

House with Cottage in quaint Brewster, Central to Cape Attractions and Beaches

Brewster, Massachusetts, United States

Sprawling, bright, renovated Cape property with a year round hot tub and bocce court in the heart of Brewster, sleeps 12 guests in 2+ bed house + 2 bed cottage within steps from one another. Walking distance to Point of Rocks and Breakwater beaches, close to bike trail,Brewster Store. Relax and get away from it all on this spacious lot on a quiet private lane, overlooking a small pond near conservation land.brbrWe lovingly renovated this home in 2019 as our vacation home, wanting to share it with guests as well to be the backdrop for cherished vacations and get togethers. brbrThe main house features a first floor king room, a sunroom with pullout sleeper, a large living area with sectional, and the kitchen/dining area is spacious enough for all with a dining table, counter island, and additional seating area. The kitchen is well equipped with dish ware and cookware. There is a full bath just off the kitchen. brThere are a few steps between the living area and kitchen/bathroom area, and a step down into the sunroom off the kitchen.brUpstairs features another king room, and just outside in the loft is a pull out full daybed that sleeps 2, along with a full bath. brThe cottage is just steps away from the main house off the back porch with a queen room downstairs and twin beds in the upstairs bedroom. The upstairs loft features additional sleeping room. There is a full bath and kitchenette and seating area in the cottage as well. brbrKEY FEATURES:br☀ Sleeps 12 in 2 Separate Structures - Main House & Cottagebr☀ Dog-friendly (limit 2 dogs)br☀ .8mi walk to Point of Rocks Beachbr☀ Central AC in Main House, AC unit in cottage (enhanced AC being added for 2026)br☀ 2 outdoor showers for summer usebr☀ Year Round Hot Tub br☀ Bocce Ball Court br☀ High speed WiFi and smart TV for streaming br☀ Bed linens, bath towels, a few bikes, and beach chairs providedbrbrbrHere Are A Few Kind Words From Our Past Guests:brbr“Beautiful home, fantastic location and clean and comfortable beds! Plenty of parking, reliable Wi-Fi, close to beaches, stores, ice cream and restaurants and a very safe neighborhood.” - Sharonbrbr“Had a lovely stay in Brewster. Great location- close to town, but still enough off the beaten path to offer privacy and tranquility. Amenities and furnishings were very comfortable and exactly as described in the listing/photos. Already talking about a potential return!” - Peterbrbr“This charming Cape Cod house is well located to enjoy all the sights of the area. It feels homey and cozy...I would stay here again!” - JaNahnbrbrbr☆☆ MAIN HOUSE ☆☆brbrThe Main House's bright and airy kitchen comes fully equipped with all the appliances, utensils and cookware you need to feel at home and cook for your group. The kitchen is open to the dining area which seats 6-8, with additional seating at the island. Located just off the kitchen is the cheery sunroom, with more lounge space located on the other side of the home in the large living room with sectional and Smart TV.brbrThe primary bedroom on the first floor is fitted with a king-size bed, with sliders to access the back deck. Also on the first floor is the separate sunroom with a queen pullout sofa. Lastly, there is a full bathroom with a walk-in shower on this floor.brbrUpstairs is the second primary bedroom, with gorgeous vaulted ceilings and fitted with a king size bed. Just outside of the bedroom is the loft area with a daybed that pulls out to a queen sleeper. The second floor sunny bathroom is located just off the loft at the top of the stairs, with a tub shower combo. Both bathrooms have been recently renovated with modern finishes. brbrbr☆☆ COTTAGE ☆☆ brbrJust steps off the back of the Main House is the Cottage, which has 2 bedrooms and 1 bath. The first bedroom is on the first floor and equipped with a queen bed. Also on the first floor is the living area with Smart TV, and kitchenette with a sink, microwave, and coffee maker. Off the kitchenette is the updated full bathroom with tub/shower combo.brbrVenture up the spiral staircase (best suited for teens and young adults) to the second bedroom, outfitted with two twin beds. There is also a living area in the loft, a great space for the kids to hang and spread out.brbrIn the summer months, the cottage is cooled with a portable AC downstairs and fans upstairs (adding AC upstairs in 2026)brbr☆☆ OUTSIDE SPACE ☆☆brbrThe exterior area of this home boasts multiple options for outdoor dining and lounging. The large back deck is equipped with table, chairs, and benches for dining. brbrA bocce ball court and available from April - Nov. Enjoy the Saluspa Hot Tub in privacy behind the cottage. Also on the back deck is the outdoor shower, available in the summer and shoulder seasons. brbrThe long private driveway offers plenty of room for parking. for up to 6 vehicles.brbrbrBook Today & Let Us Take Care Of You In Brewster!
Bed 4

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Bath 3

Bath

Sleep 12

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Exceptional(7)

$580.35

/ Nightly
Private Vacation Home

Delightful, dog-friendly home with private deck, grill, outdoor dining & WiFi

Brewster, Massachusetts, United States

Haven CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrAn enchanting stay awaits at this charming, split-level vacation home, perfect for extended families who want to vacation together but still have separate living spaces for privacy! Highlights include a fantastic private backyard, ample space for the whole family, and your own patio with a grill. There's a well-equipped kitchen with dining seating for eight. Spend gorgeous days in the sun on nearby beaches, with a beach umbrella even provided for your use.brbrYou'll love the feeling of seclusion while being close to all the incredible shopping, dining, and activities the Brewster area has to offer. Enjoy being close to the bike trail, an array of great beaches, golf courses, putt-putt courses, whale watch excursions, and saltwater fishing opportunities. If you're brining your rod and reel, Nickerson State Park also has some of the best freshwater fishing on the Cape.brbrTHINGS TO KNOW brThis is a split-level home with separate entrances, kitchens, bedrooms, TVs, and sofas on the upper and lower levels.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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 4

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Bath 2

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Sleep 10

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Exceptional(47)

$589.42

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Private Vacation Home

Picturesque Private Beachfront House on Cape Cod Bay

Brewster, Massachusetts, United States

If you can imagine the perfect family summer vacation at the sea, you can find it at our bay-side Cape Cod cottage! The 1950's style house is located on a high bluff in East Brewster overlooking the Cape Cod Bay. The views are unbelievable; the vista is constantly changing along with the colors of the water and the clouds. You can watch a storm roll in and experience a rainbow.brbrWe are located in East Brewster, known for the lowest tides on Cape Cod - at low tide, the water retreats for a mile and a half! You can go for a bracing early morning swim, or wait till the tide is high at night when the water is warmer than the air, and it's just you floating under the stars. At low tide you can explore the 'flats' and the creatures that live on and under them: razor clams, quahogs, hermit crabs, sand crabs, snails, minnows, and horseshoe crabs. Families play frisbee, volleyball and wiffle ball on the flats and the bay is ideal for swimming, sailing or water-skiing.brbrThe house itself has been maintained and loved by the same family for 50 years. Although it sleeps up to 11, it has a warm and cosy feeling. You can safely walk or ride your bike to any number of restaurants, coffee shops and stores. You may choose to spend your whole time at 35 Dune Road (you'll find once you're there, you don't want to leave) or you’ll have the whole of Cape Cod to explore!br
Bed 4

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Bath 2

Bath

Sleep 10

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Home Most popular vacation rentals in Brewster