Vacation Home Rentals By Owner In Chatham, MA

Enjoy your vacation at this lovely North Chatham home. This charming, sunny and spacious, arts and crafts bungalow is completely renovated with hardwood floors throughout. The light and airy kitchen is updated with stainless steel appliances and granite counter tops.....perfect for entertaining. A window-filled sun room offers extra living space where you can relax, have your morning coffee,and enjoy the singing birds.brbrThe attention to detail in decor and beautiful woodwork makes this home very special and warm. Central AC, cable TV, Internet, dishwasher, washer/dryer, BBQ grill, and an outdoor shower.brbrTwo outdoor decks allow you to appreciate the beautiful and spacious yard. The upstairs deck off the master bedroom even has peeks of the Chatham Harbor. This a perfect walking neighborhood, too. Take a quick stroll to Cotchpinicut and Scatteree Beaches less than a 10 minute walk away. brbrIt's a great spot to begin your Cape Cod vacation memories in. Schedule today and plan to enjoy your stay.

Quiet North Chatham 4 Bdr 2 Bath Large Lot Outdoor Shower Complete Remodel

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$602.17

Summary:brbr16619 - Chatham Cruiser: On the Chatham Loop - 1 Min to the Beach!brbrbrbrThe Space:brbrChatham Cruiser is the perfect mix of modern comfort and historic charm, offering a classic Cape Cod summer experience. brbrStart your day in the beautiful kitchen, and once breakfast is ready, sit down in the sun-soaked breakfast nook for the most important meal of the day. Relax in the bright living room before heading on a nice stroll through the gorgeous Chatham neighborhood to get to Oyster Pond Beach - the perfect place to take the kids for the day. Main Street is also just down the road, where you will find plenty of options for dining, shopping, and entertainment. br brReturn home to the patio in the back, under the shade of the Japanese cherry tree. Serve up BBQ and evening cocktails, with the large, fenced-in yard being a great space to play lawn games, entertain, and regroup to go out and enjoy some evening fun at the many beaches or restaurants close by. Retire for the evening to one of the five bedrooms, all with air conditioning to beat the summer heat. The primary bedroom has a queen bed, with another queen bed on the second floor, twin beds in bedrooms 3 and 4, and two twin beds in the final, fifth bedroom. brbrOther amenities include an outdoor shower, propane grill, washer/dryer, multiple TVs with cable, and numerous indoor and outdoor dining options. Staying at Chatham Cruiser, you will feel the stories this home has experienced, and can excitedly add to the rich history of this Cape gem. brbrHome Details:br-No Pets(Fines Remitted)br-Sleeps 8br-2 FloorsbrBedroomsbr-Total 5br-1st Floor Bedroom: 1 Queen Bedbr-1st Floor Bedroom: 1 Twin Bedbr-2nd Floor Bedroom: 1 Queen Bedbr-2nd Floor Bedroom: 1 Twin Bedbr-2nd Floor Bedroom: 2 Twin BedsbrBathroomsbr-Total 2br-1st Floor: Full Bathroom w/ Shower/Tub combobr-2nd Floor: Full Bathroom w/ ShowerbrOther Amenitiesbr-Fully Equipped Eat-In Kitchenbr-4 Mini-Split A/C Units + 2 Window A/C Unitsbr-Smart Lockbr-TVbr-WiFibr-Washer/Dryer (1st floor)br-Patio w/ Outdoor Diningbr-Propane Grillbr-Outdoor Showerbr-Private Fenced-In Yardbr-NO Pets (fines remitted)br-Located on the Chatham Loopbr-Minutes to Oyster Pond Beach & Main Streetbr-Sheets and Bath Towels Provided with Beds Made Upon Arrivalbr-Cleaned with Hospital Grade DisinfectantbrC0409890550brbrbrbrThe Neighborhood:brbrOceanside

On the Chatham Loop - 1 Min to the Beach!

Chatham, Massachusetts, United States

5

Bed

2

Bath

8

Sleeps

$1629.4

This property is professionally managed by Pretty Picky PropertiesbrbrExquisite Chatham Home, Easy Access to Town, Bike TrailbrbrSleeps 10br4 Bedrooms plus flex bonus room, 3.5 BathroomsbrRents Friday to Friday during peak seasonbrLinens Included. Beds made.brPets consideredbrbrPool & Hot Tub open from Memorial Day to Columbus DaybrbrLooking for a luxurious way to experience Chatham Look no further! New to the rental market, this 4 bedroom 3 and a half bath home is ideally set up to welcome groups of up to 10. Built in 2012, this modern home has all the creature comforts you'd expect from a luxury level home. The open floor plan features a fully equipped chef's kitchen that is open to the dining room and the vaulted living room that is flooded with natural light from the sky lights. There is a screened porch off the back that leads out in a beautiful new pool area! The heated salt water pool will have a gorgeous patio area with ample seating and lounging area. There will also be a large 6-person hot tub in the pool area. brbrBack inside, you'll find the spacious primary bedroom with a King bed and an adjoining gorgeous private bathroom with a dual vanity and tile and glass step-in shower. Finally, there is a small room with a twin bed to round out the main level. Upstairs you have a classic Cape set up with a full bathroom at the top of the stairs and a bedroom on either side. The first bedroom has a King bed and the other has three twin beds. brbrBut wait, there's more! The fully finished lower level has a TV lounge, a wet bar and a table for games or cards. There is another guest room with office space and one additional room down here for flex sleeping space with queen beds in each. There is a full bath in the lower level as well.brbrThe house is under a mile from Chatham Village for shopping, dining, and browsing. You're even closer to the Chatham Angler's baseball field for Cape League action. Want to explore by bike There is access to the bike trail less than 1000 feet from the house. Pets are considered so the whole family can enjoy some time in Chatham! brbrPlease enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrThis property offers a 3-night minimum outside of the peak season. Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7-nights or more and the cleaning fee is waived.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod.brbrPlease enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00br In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.brbrThis property offers a 3-night minimum outside of the peak season. Guests are charged a cleaning fee for all stays less than 7 nights. Stay 7-nights or more and the cleaning fee is waived.brbrBe sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. brbrIt's your vacation. Get Picky! ® brbrTown of Chatham Registration #1095

Barefoot Bungalow: 330-C Exquisite Chatham Home, Easy Access to Town, Bike Trail

Chatham, Massachusetts, United States

4

Bed

Bath

10

Sleeps

$617.95

Short walk to Ridgevale Beach! This 3 bedroom house (king, 4 twins) and 2 full baths allows plenty of space for the entire family. Full kitchen and dining area, large living room with 2 of the bedrooms on the first level. An extra family room on the lower level with an additional TV and the 3rd bedroom. Spend the morning with your cup of coffee on the deck before heading to the beach for the day, or enjoy a delicious BBQ after a fun day in the surf and sand. Enjoy the outside shower, its great for rinsing off the salt and sand. Central A/C and wifi keep you cool and connected, and flat screen TVs with cable and streaming, are perfect for watching summer baseball and movies on those rainy days. Dog friendly too, pet fee of $150 will be added to the lease (1 dog allowed). This home comes with a Welcome Bag: a reusable tote with a starter pack of cleaning and paper products, all compliments of the owner. Call Chatham Rentals today and let us help you plan your visit!

Family Tides Ridgevale Beach Getaway!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$956.92

This property is professionally managed by Pretty Picky PropertiesbrbrUpdated Chatham home with access to private beachbrbrSleeps 10brFour Bedrooms, Three Full BathsbrRents Friday to Friday during Peak SeasonbrLinens Included, Beds MadebrbrNestled atop one of the highest point in Chatham, this remarkable vacation rental property promises an enchanting getaway for families and friends alike. With four beautifully appointed bedrooms and three modern bathrooms, this spacious home comfortably accommodates up to ten guests, making it ideal for large gatherings or family retreats.brbrThe ambiance is warm and inviting, featuring a blend of contemporary design and cozy touches. You'll love the open-concept living area, which is perfect for entertaining or relaxing after a day of exploration. Natural light floods the space, and with a garden view.brbrKey features include a well-equipped kitchen, complete with modern appliances such as a refrigerator, microwave, and coffee maker, along with ample dining space for shared meals. Enjoy evening entertainment in the game room that boasts a pool table, board games, and video games for all ages.brbrStep outside to discover a backyard oasis, featuring a hammock chair, outdoor seating, and a fire pit for cozy evenings under the stars. Adventurers will appreciate nearby lake access for kayaking. A spacious deck offers the perfect setting for outdoor dining, allowing guests to enjoy warm summer nights surrounded by nature.brbrAdditional amenities include air conditioning for comfort, WiFi to stay connected, a washer and dryer for convenience, and a smart TV for entertainment during downtime. Safety features such as smoke detectors and a first aid kit ensure peace of mind throughout your stay and checked regularly.brbrLocated in the picturesque neighborhood of Lovers Lake, guests can easily explore charming Chatham and enjoy nearby beaches, bike trails, and local shops. Don't miss the opportunity to create unforgettable memories at 048-CH—your dream vacation home awaits!brbrPlease enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $215.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. brbrIt's your vacation. Get Picky! ®

Over The Horizon: 048-CH Updated Chatham home with access to private beach

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$437.88

Chatham CharmerbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrRelaxation and outdoor fun await at this charming Chatham house. Located just 0.3 miles from Ridgevale Beach, this home is also just a few miles away from Chatham, where you'll find the Orpheum Theater, a playground, Chatham Anglers baseball, seal tours, shopping options, and tasty restaurants to sample.brbrThe house itself includes a number of features everyone is sure to appreciate, such as ocean views, a washer/dryer, central AC, internet, and a gas grill for outdoor cooking. Experience cozy nights in with your favorite shows or a movie using the DVD player, or catch up on some reading from one of the provided books. With a hammock outside, comfortable chairs around the firepit, and alfresco dining on the furnished deck, you'll have plenty of opportunities to unwind and enjoy the fresh ocean air. brbrFor your entertainment needs, you will find two TVs with Fire Sticks, perfect for accessing your favorite streaming services during your stay. Prefer your own device Feel free to bring along your Roku, Apple TV, or any other streaming stick. The living room also features a sound bar, ideal for enjoying music or creating a theater-like experience for movie nights. brbrThings to KnowbrbrParking notes: There is free parking available for 3 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.

Water-view house near golf with firepit, grill, deck, central AC & washer/dryer

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$472.16

The Sea StarbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrConveniently located on a private lane set back from the main road and only a 1/3 mile walk to Forest Beach, this sunny home offers the perfect home base for a relaxing and unforgettable vacation with your family and friends! Forest Beach offers approximately one mile of pristine beach and its parking lot does not require a sticker. Find public tennis and basketball courts down the path adjacent to the house. Other great local attractions and places to visit include downtown Chatham, Harwichport, Cranberry Valley Golf Course, Chatham Lighthouse, Monomoy National Wildlife Refuge, Nickerson State Park, Pirate's Cove Adventure Golf, The Music Room Cape Cod, and South Chatham/South Harwich Woods.brbrThis family-friendly home is all about outdoor living with an enclosed backyard featuring a large lawn, a firepit surrounded by comfy Adirondack chairs, and a grilling area with a gas grill and an outdoor dining table with an umbrella to protect you from the sun. The front patio enjoys additional seating and an enclosed outdoor shower for rinsing off the sand after a memorable day at the beach.brbrInside, discover a welcoming living room boasting a smart TV with streaming and cable services, and comfy sofas throughout. Spend entertaining evenings streaming your favorite shows with your loved ones! When it's time to eat, surprise everyone with a favorite recipe prepared in the well-appointed kitchen, complete with modern stainless steel appliances. There is a rec room with a second smart TV for folks who would rather watch another movie or series. Additional perks include a stacked washer/dryer, board games, two beach chairs, coolers, and yard games.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.brbr-Fireplace is Not For Guest UsebrbrIf 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 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.

Home near beach & tennis/basketball court with firepit, grill, & patio

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$696.43

Mill Pond VistabrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrTake in gorgeous views of Mill Pond from sunrise to sunset at this waterfront home in the tranquil woodlands of Chatham. Serene and spacious, this is a place for quiet mornings spent sipping coffee on the lake-facing deck, and fun-filled afternoons of swimming, canoeing, and fishing with your loved ones.brbrThis 2,176-square-foot home sits on the north shore of Mill Pond, with direct access to the water from the property. It's a memorable retreat for a family or a group of friends, with downtown Chatham easily reachable four miles east. You'll also be wonderfully close to Hawksnest State Park (one mile), the Old Colony Rail Trail (two miles), Forest Beach (three miles), Ridgevale Beach (three miles), and Lighthouse Beach (five miles).brbrThe house is a natural space for gathering, with its open layout, large rooms, and comfortable furnishings. Bring a glass of wine out to the sun porch, prepare summer lobsters in the expansive eat-in kitchen, or light the gas grill to sear local seafood on balmy evenings. When the nights turn cool, flip on the gas fireplace and find a good movie to watch on the living room's 60-inch HDTV with Amazon Prime Video, Apple TV, and Chromecast.brbrThree spacious bedrooms, a Pack 'N Play, and central air conditioning ensure your nightly comfort. You'll also have a washer/dryer, generous closet space, and complimentary WiFi for your convenience.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.brbrParking notes: There is free parking available for 4 vehicles.brbrSecurity camera details: There's a security camera at the front door.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.

Waterfront home with lovely lake views, great deck, sun porch & fireplace

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$852.65

Relax and revive in this airy, modern and beautifully appointed 2400 square ft. Cape Cod home in a lovely secluded neighborhood with spectacular stone patio, deck & garden. Just three quarters of a mile to peaceful fresh water swimming or paddle boarding on Schoolhouse pond, 1 mile from Pleasant Bay and Jackknife beach, and a 7 min drive to both downtown Chatham and Nantucket Sound beaches (Harding's Beach is our favorite). Close to the lower cape’s scenic paved bike trail, the neighborhood’s winding roads have very little traffic and are perfect for early morning runs or leisurely evening strolls.brbrBeautifully renovated dine-in chef's kitchen with sea glass wall tiles, granite bar and island, wide plank pine floors, double convection ovens, induction cooktop and a wall of windows opening onto the deck and overlooking the landscaped stone patio and surrounding woods as well as a pollinator garden haven for monarchs and hummingbirds. Dining area with airy cathedral ceiling opens onto the deck.brbrEnjoy grilling on the stone patio (Weber gas grill) in the beautifully landscaped back yard partially surrounded by woods. Looking down on the patio is a multi-level deck lined with giant hydrangeas and pollinator gardens featuring comfortable outdoor furniture and multiple umbrellas, perfect for outdoor dining, stargazing or lounging with a book.brbrEn Suite queen bedroom on the ground floor with renovated glass and marble walk in rain shower. Second bath with tub and shower with sea glass tile downstairs. Upstairs is a King bedroom, and light filled cathedral ceiling queen master bedroom with skylights and adjacent 3rd newly renovated bath with walk in shower. In addition to central air conditioning, all bedrooms have ceiling fans. brbrHigh speed wifi. Large flat screen smart TVs in the living room and finished basement level have expanded cable. The spacious carpeted basement level also has a desk and wireless printer. Sheets and towels and beach towels are included - Beach chairs and umbrellas available as well. Grocery store and CVS are a 5 minute drive. Plenty of parking in long circular driveway. brbrPlease note this house is not ideal for young children. brFor your safety, enhanced cleaning protocols are remain in place.

New July dates! Sun drenched Cape haven- spectacular deck, garden & patio!

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$2031.49

Enjoy all Cape Cod has to offer with this beautiful sea captain's house centrally located in Chatham, MA. Less than 1 mile to town and a short walk to the beach. Comfortably sleeps 10 people. Includes all amenities to cook delicious meals, wash clothes, comfortable beds, high-speed WiFi, Cable, located in a quiet neighborhood with space to park 4 vehicles in the driveway. Hardwood floors, lots of windows, a beautiful deck, and an attached 3-season porch overlooking the backyard and conservation land.

Large Chatham Home Overlooking the Atlantic

Chatham, Massachusetts, United States

Bed

Bath

12

Sleeps

$1108.39

We are delighted to present a beautiful antique Greek Revival home located on the Chatham Loop, perfect for your next vacation. This spacious yet cozy rental features four bedrooms and comfortably sleeps ten guests. The property offers two primary bedrooms with king beds on the first floor. Upstairs you'll find two additional bedrooms furnished with two queen beds and two twin beds, making it ideal for extended families. The home boasts a grand family room and an extra den, providing ample space to relax and unwind. Gather for family meals in the cathedral-ceiling dining room filled with natural light, or use the smaller dining room for additional seating. The modern, updated kitchen conveniently leads to the backyard and deck. Outside you'll discover an exceptional entertaining oasis with lush, grassy yards and fragrant seasonal plantings. Enjoy grilling dinner under the stars or take a short walk into town for a movie, a baseball game, or ice cream. After a day at Oyster Pond or Lighthouse Beach, wash off the salt and sand in the enclosed outdoor shower. For your comfort, window air conditioning units are provided in the common areas, and Wi-Fi keeps you connected. Upon check-in, you will receive a complimentary Welcome Bag from the owner stocked with starter cleaning and paper products.brThis is a truly special rental, offering a wonderful setting to create lasting Cape Cod vacation memories year after year. Contact Chatham Rentals today and let an experienced rental agent help you plan your stay.

Beautiful antique Greek Revival home located on the Chatham Loop

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1440.52

Spend your Cape Cod vacation in this rental perfectly situated in the heart of downtown Chatham. We're just a half-mile from the sandy shores of Nantucket Sound and Lighthouse Beach. The expansive backyard and new patio are ideal for sunbathing or a game of croquet, so bring your set! The beautiful, bright, and new living room and large dining room create the perfect space for entertaining. This home features one queen bed, seven twin beds, and a set of bunk beds. Start your day with a cup of coffee on the front porch as you plan your adventures. In the evenings, relax on the patio under the stars before heading into town for dinner and a movie. Don't forget to grab ice cream or visit The Candy Manor for dessert and a bit of shopping! The main house has central A/C, and the attached cottage includes one window A/C unit. There is parking for three cars. This is a wonderful vacation spot for creating lasting family memories with BBQs, days spent collecting shells on the coast, and enjoying ice-cold lemonade on the front porch. It's a charming home you'll want to return to year after year, making new Cape Cod vacation memories. Upon arrival, guests will receive a Welcome Bag containing a reusable tote starter pack filled with essential paper and cleaning products for their stay. **Important Parking Note:** Parking is permitted for up to three vehicles, but only in accordance with the Parking Restrictions and Parking Instructions. Please speak with your agent for further details. Call us at Chatham Rentals, and let us help you plan your stay!

Vacation in downtown Chatham close to Lighthouse Beach

Chatham, Massachusetts, United States

Bed

Bath

11

Sleeps

$552.83

90 mile (mostly highway) drive to Gillette Stadium, where some 2026 World Cup Games will be held. Enjoy a vacation in desirable Chatham during your trip!Cape Cod style home with a large, private yard, sunny deck, outdoor shower and hammock in a quiet Chatham neighborhood. brbr• Great Location!brThis is a great home base for your adventures in Chatham and Cape Cod. Centrally located but still quiet, private, lovely vacation spot near nice beaches, the bike path, walking areas, excellent shopping and restaurants. The house sits in a quiet area on a dead-end road to Oyster Pond, with no through traffic or public access. 3 minute walk down “The Garden Path”, a grassy path that runs from the house to the local fish market, deli, natural food store, pizza and favorite restaurants, Mac’s Seafood and Pate’s. Walk, bike or drive 1.3 miles to downtown Chatham, 1.7 miles to renowned Hardings Beach and more.brbr• Perfect for days at the beach.brWe have everything you need: beach chairs, sand umbrella, beach towels, sand toys and cooler. Chatham has quite a variety of ocean and fresh water beaches. Renowned Hardings Beach is a short 5 min drive away. Outdoor shower and a clothes line make trips from the beach easy. brbr• Relax in the yard or on the deck.brHang in the hammock to nap or read in the shade. Play games in the large, private yard, suitable for family soccer, wiffleball, bocce and croquet games that are fun for all ages. Have a meal, entertain or just relax on the deck. The deck has comfortable furniture, dining table and a large gas grill. One of our favorites is to explore “The Garden Path”, a grassy path that runs from the house toward Oyster Pond.brbr• Everything You Need.brFully stocked kitchen, full size laundry, grill and shed with beach paraphernalia and lawn games. There are some other helpful items in the house such as binoculars, books with local activities and history, maps and information about local activities, etc. Smart TV access to your streaming accounts like Netflix, Hulu, Peacock, etc.brbrAll linens included.

See the World Cup AND Enjoy a Chatham Vacation June 2026

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$558.22

Corner CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrCharm, wonder, and fun await in Chatham. This family-friendly home, that's been in the owner's family since it was built, is located near the Old Colony Rail Trail (an excellent neighborhood bike trail), Forest Beach, Chatham Center, and Harwich Port Center. Beautiful sites and delicious bites are not hard to come by in this area - so explore it for all that it's worth and enjoy every second! brbrInside your cozy quarters, you will gleaming hardwood floors, comfortable furnishings, and a lovely outdoor hang-out space. Play a board game in the spacious main living room. Cook up something tasty in the well-equipped kitchen. And rest easy come nightfall thanks to the home's soft bedding and partial air-conditioning. brbrFamily time is of the utmost importance during your stay, so practice your barbecuing skills on the provided grill and serve your creation to those you love, as you relish another day spent together, under the Massachusetts sun. brbrTHINGS TO KNOWbrbrParking notes: There is free parking available for 3 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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Friendly retreat with a deck, AC, and board games - stellar central location

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

Select Dates for Price

Nestled at the end of Little Beach Road in Chatham, this charming 3-bedroom, 2-bathroom cottage invites you to indulge in coastal bliss. With accommodation for up to 6 guests, it promises a cozy retreat amidst Cape Cod's breathtaking scenery.brStep directly from your doorstep down the path to the pristine sands of one of Cape Cod's most picturesque waterfronts, where days are spent basking in the sun and frolicking in the azure waters. As the sun sets, immerse yourself in the vibrant pulse of downtown Chatham, just moments away, offering a plethora of world-class shopping and dining options.brReturn to your haven in the evening and delight in the simple pleasure of grilling dinner while being serenaded by the gentle symphony of the sea. Rest assured, with air conditioning units in each bedroom, balmy summer nights are met with cool comfort. Experience the allure of a lifetime in this unparalleled destination. Don't let this opportunity slip away—seize the moment and make memories to last a lifetime.brSubject to applicable taxes and fees. All 2025 bookings are 7 night minimums, Sat. to Sat. only. Tenants provide their own linens and towels. No pets, please. 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.

3 Bedroom Sea-Side Cottage w/ Beach Access RPAM083

Chatham, Massachusetts, United States

Bed

2

Bath

Sleeps

Select Dates for Price

Nestled at the end of Little Beach Road in Chatham, this charming 2-bedroom, 1-bathroom cottage invites you to indulge in coastal bliss. With accommodation for up to 4 guests, it promises a cozy retreat amidst Cape Cod's breathtaking scenery.brStep directly from your doorstep down the path to the pristine sands of one of Cape Cod's most picturesque waterfronts, where days are spent basking in the sun and frolicking in the azure waters. As the sun sets, immerse yourself in the vibrant pulse of downtown Chatham, just moments away, offering a plethora of world-class shopping and dining options.brReturn to your haven in the evening and delight in the simple pleasure of grilling dinner while being serenaded by the gentle symphony of the sea. Rest assured, with air conditioning units in each of the bedrooms, balmy summer nights are met with cool comfort. Experience the allure of a lifetime in this unparalleled destination. Don't let this opportunity slip away—seize the moment and make memories to last a lifetime.brSubject to applicable taxes and fees. All 2025 bookings are 7 night minimums, Sat. to Sat. Tenants provide their own linens and towels. No pets, please. An administrative fee and applicable taxes may apply. This property does not have air conditioning.

2 Bedroom Sea-Side Cottage w/ Beach Access RPAM085

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$357.35

A Chatham Pearl on Oyster RiverbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrExperience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach.brbrThis quaint two-level home is scenically situated between Nantucket Sound and Oyster Pond, creating a wonderful retreat for beach-goers, families, and water sports enthusiasts. It's also only one mile from Harding's Beach, two miles from downtown Chatham, and three miles from Oyster Pond and Forest Beaches. brbrStep inside this architect's residence to find a lovingly renovated interior, which features an open floor plan, hardwood floors, and comfortable white furnishings. Come home from the beach to cool off by the portable air conditioner, browse the WiFi, or watch your favorite show on one of the two flatscreen cable TVs. brbrYou'll find butcher block countertops, modern appliances, and even a sound dock in the open kitchen, while the farm table provides dining space for six. The wrap-around deck also offers a grill, patio seating, and glorious views of the river below.brbrAs you head out the door to the beach each morning, be sure to bring along the provided beach chairs and toys. One dog is also welcome to join you here, but please note that a 20-pound weight limit.brbrThis three-bedroom, two-bathroom home will sleep as many as six guests. You'll find a queen bed in the master bedroom, two twin beds in the second bedroom, and a set of twin bunk beds in the cozy third bedroom. Additional amenities include a Pack 'N Play, a washer/dryer, and a selection of board games.brbrWhether you're an annual visitor to Cape Cod or planning your first summer getaway, the town of Chatham is beloved throughout New England. Soak in the sun and take a refreshing dip at Forest, Harding's, and Oyster Pond Beaches; spend an afternoon window shopping in downtown Chatham; and soak in the all-American atmosphere at a Chatham Anglers game at Veterans Field.brbrThe natural beauty and charm of Cape Cod can be all yours - book your stay at this unforgettable Chatham home today!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 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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham, Massachusetts, United States

Bed

Bath

Sleeps

$1828.04

Beautifully renovated in 2020, this historic Chatham home is steps away from Lighthouse Beach. Bright and airy, the open 1st floor makes for easy entertaining. A chef's kitchen with a large granite island is great for your family breakfast before walking to the beach for the day. 5 bedrooms that can sleep 10. Enclosed outdoor shower to wash the sand away after hours in the surf and sun. Family room, dining room and an extra sitting area offer tons of space to relax in. First and second floor decks boast lovely views of blue skies and blue water. Another short walk brings you to downtown Chatham for shopping, dining and entertainment. Jump on the Chatham Loop for your morning walk too! Gas grill for cooking dinner under the stars, central a/c to keep you cool on those hot summer days, TV with streaming services only, and 300 DPI Wi-Fi to keep you all connected, Welcome bag included...your starter pack of cleaning and paper products needed for your visit. Call Chatham Rentals today, and let an experienced agent help you plan your visit. br**The auxiliary apartment is reserved for the property manager's use only. The manager is not on-site during tenant stay unless an emergency maintenance issue arises.**

Historic Chatham house was moved from Water Street to present location in 1872 to avoid destruction by the salty tides.

Chatham, Massachusetts, United States

5

Bed

2

Bath

10

Sleeps

$1182.22

Located in Chatham, enjoy what this 3-bedroom house has to offer. Guests will find a welcoming space featuring one king bed, one queen bed, and two full beds, perfect for a restful night. With four bathrooms, including a soaker tub, comfort is never far away. The house stays cozy with heating and cool with AC, making it a tremendous choice year-round. Whether relaxing indoors or exploring nearby, guests will appreciate the gorgeous surroundings and thoughtful details throughout. We hope you'll enjoy your stay at our house. The home is located within 5 minutes to downtown as well as the beach. The neighborhood is beautiful and quiet perfect for walking around and spending time with family. The property sits with plenty of privacy on a large lot for Chatham.

Wonderful renovated 3-bedroom house with AC in quaint Chatham

Chatham, Massachusetts, United States

Bed