House vacation rentals in Chatham

The main living area features white slipcovered sofas surrounding a central coffee table, with a cozy electric fireplace situated beneath a wall-mounted smart TV. Large windows provide ample natural light and a view of the outdoor space, enhancing the room's bright ambiance.

5 out of 5 average rating, 51 reviews

Downtown Chatham Home w/ Patio - Near Oyster Pond

This stunning historical home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, Oyster Pond, movie theater, Veterans Field for Chatham A’s games & more! This cozy home is perfect for a family, group of friends, or couples with two living areas, an outdoor patio with lounge areas, a large dining table, grill & fire pit. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

A spacious roof deck features a dining table with seating for eight, shaded by a vibrant red umbrella. A lounge area showcases comfortable seating against a backdrop of a beautiful sunset. A grill and a cornhole game add to the outdoor enjoyment.

5 out of 5 average rating, 12 reviews

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

4.95 out of 5 average rating, 311 reviews

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

A charming beach house with shingle-style siding is displayed, set within a landscaped yard. Two large bushes frame the entryway, and the building features multiple rooflines and skylights. A brick pathway leads to the front door, with trees providing partial shade in the foreground.

4.96 out of 5 average rating, 112 reviews

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

A modern kitchen features stainless steel appliances and a tiled backsplash, with a clear view of the adjoining dining area. Soft overhead lighting illuminates the space, complemented by hardwood flooring. A large window allows natural light to enhance the inviting atmosphere.

4.95 out of 5 average rating, 100 reviews

Spacious Pet Friendly Cape, Large Yard

Our home is located in a quiet neighborhood close to beaches, golf courses and bike trails. It is a short drive to Chatham town center and is the perfect location to be close to all attractions but secluded enough to unwind. Take advantage of the outdoors on a new deck and large backyard. Large, mature plants and trees surround the property on three sides. Blackberry, raspberry and blueberry bushes in the backyard provide ripe fruit in the summer months.

4.96 out of 5 average rating, 52 reviews

Walk to beach/Main Street/bike path/dog friendly

Welcome to your North Chatham escape — a comfortable, coastal 2-bedroom home with central A/C, a fully fenced yard, and an outdoor shower for easy beach days, with beach chairs and umbrella. Take a 15-minute walk to the beach, then enjoy quiet evenings at home grilling on the patio, or a quick trip into Main Street Chatham, just 1.2 miles away. Perfect for couples, small families, and guests traveling with dogs.

A serene view of a calm harbor filled with various boats, all anchored in the water. The foreground features a grassy area with a wooden path leading toward the water's edge, while vibrant greenery and flowers are visible along the border.

4.97 out of 5 average rating, 101 reviews

Oceanfront Chatham Village Home

Quiet Peaceful Oceanfront Home, Short Walk to Chatham Village and Walk to Lighthouse Beach. Sleeps 12. Large kitchen, stainless steel appliances, gas stove. Every Room except one room has amazing ocean views! Stone patio overlooks Ocean Harbor on Little Mill Pond. A Video Walkthrough of the house, featured by Eileen Cotter of Pure Wander: https://www.youtube.com/watch?v=_tqi6m8-1zs&t

The exterior of the renovated Chatham home features a white picket fence and a gravel driveway. The house showcases a gabled roof and large windows, surrounded by greenery and trees. The clear blue sky above emphasizes the peaceful neighborhood setting.

4.92 out of 5 average rating, 202 reviews

Quaint Downtown Chatham Home

This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

A welcoming entrance is framed by a white trellis, lined with dense green foliage. The pathway leads to a charming house with a light-colored facade and a central front door, flanked by outdoor lighting fixtures and neatly trimmed shrubs.

4.94 out of 5 average rating, 196 reviews

Close to everything in Chatham

3 bedrooms ( 1 King bed, 2 Queen beds, 2 Twin beds and a Queen sofa sleeper), 2 1/2 baths, sleeps 8, 3 levels of living space with Queen bed downstairs, yard and patio, deck bbq, lounge chairs, large patio table with umbrella, outdoor shower and washer and dryer.

4.98 out of 5 average rating, 519 reviews

The charming front exterior of a gambrel style cottage is visible, featuring shingled siding and a symmetrically gabled roof. Flower boxes are positioned beneath the windows, showcasing vibrant plants. A welcoming dark front door is centered, flanked by two tall, lush evergreens.

Home in West Harwich

cape cod riverview cottage

This is a 8 year old gambrel style custom Cape Cod shingled guest cottage is surrounded by lush landscaping and a beautiful view of a tidal river. The river leads to the ocean and is available for canoeing, sailing and kayaking.

The exterior of a charming cottage is surrounded by vibrant flowering bushes, featuring large blue and pink hydrangeas. The cottage displays a shingle facade, white windows, and a small decorative chimney, with a pathway made of pebbles leading to the entrance.

4.96 out of 5 average rating, 217 reviews

Studio cottage in Chatham Ma.

Comfortable studio cottage perfect for 1-2 people, queen bed, full bath with shower, kitchenette and outside shower when you come from the beach. Gas grill, brick patio with pergola and close to all that the cape has to offer.

A charming cottage exterior is visible, featuring a gray shingle facade and a red brick chimney. Lush green shrubs and blooming hydrangeas line the pathway, leading to a welcoming entrance. The sunroom is situated to the left, showcasing windows that enhance natural light.

4.99 out of 5 average rating, 189 reviews

Chatham Charmer

Lovely bright and cheery 2 bedroom 1 bathroom updated cottage in Chatham. Centrally located: around the corner from the bike trail, 1 mile to town, and 2.5 miles to the beach. Come escape to the Cape.

Popular amenities for Chatham house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.78 out of 5 average rating, 37 reviews

An inviting outdoor space is depicted, featuring a spacious in-ground pool surrounded by lounge chairs. String lights are strung across the pool area, illuminating the backyard. A pool house and umbrellas provide additional amenities, while the home's facade is visible in the background.

Home in Barnstable

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!

4.91 out of 5 average rating, 34 reviews

The backyard features an inground pool illuminated at night, surrounded by wooden decking. Nearby, a shed with white shutters enhances the outdoor space, while lush greenery provides a serene backdrop.

Home in Orleans

5-bedroom Cape with a pool and yard games.

4.82 out of 5 average rating, 11 reviews

A fenced backyard with a sparkling pool is surrounded by a manicured lawn and blooming shrubbery. Lounge chairs are positioned near the water, inviting relaxation. The home features a two-story design, with windows overlooking the outdoor space and wooded area in the background.

Home in Falmouth

Overlook Poolside Getaway Heated Pool (May - Oct 2

4.88 out of 5 average rating, 24 reviews

The exterior of the home is presented with natural wood siding, complemented by green shutters. Solar panels are mounted on the roof. A welcoming front porch leads to the main entrance, while a garage is visible to the left amidst well-maintained landscaping.

Home in Harwich Center

4 BD slice of Harwich Heaven

4.92 out of 5 average rating, 50 reviews

A spacious outdoor area is highlighted by a seasonal heated pool surrounded by a wooden deck. Multiple blue lounge chairs are arranged around the pool, and a fire pit table is situated at the center. A large checkers board and garden beds add to the inviting atmosphere.

Home in Yarmouth Port

Winslow Acres [heated] Pool Escape; pool May-Oct

4.87 out of 5 average rating, 15 reviews

The lighthouse features a round white structure topped with a lantern room. A spacious deck wraps around the building, accompanied by a well-maintained lawn and a decorative pumpkin. American flags are displayed, and the surrounding area includes additional nearby structures and views of the water.

Home in West Dennis

Jolly Captain Lighthouse

4.95 out of 5 average rating, 130 reviews

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

Private Pool, near beaches, 3 BR/3 BA, Central Air

5 out of 5 average rating, 11 reviews

A large outdoor pool area is framed by lounge chairs and umbrellas, providing ample seating for relaxation. The pool itself reflects a clear blue sky, while a shaded seating area offers cover at one end. The scenery features well-maintained paver stones surrounding the pool.

Home in Hyannis Port

Townhouse on the beach, pool, walk to Main St.

Weekly house rentals

The outdoor patio area features a large dining table surrounded by chairs, alongside a cozy fire pit with seating options. Lush greenery and a tree provide shade, while the property’s exterior showcases a charming design. Steps lead to an elevated deck area.

5 out of 5 average rating, 26 reviews

Downtown Chatham Walk to Everything: 4 Bedroom+

4.92 out of 5 average rating, 75 reviews

Chatham Coastal Escape Outdoor Living/Shower AC

The exterior of a charming summer home is depicted, featuring a light grey shingle facade and distinctive yellow door. Lush green grass surrounds the property, with flowering shrubs positioned along the walkway. Multiple windows line the front, allowing for ample natural light.

4.98 out of 5 average rating, 91 reviews

Chatham House Near Town and Beach

A functional kitchen features light-colored tile flooring and wooden cabinetry. A double sink is positioned beneath a window, and a stove is located adjacent to a refrigerator. Counter space is available on both sides, with additional storage cabinets visible.

4.92 out of 5 average rating, 52 reviews

Chatham Beach Cottage

The exterior of the Sea Captain's House showcases a charming shingle-style design, set within a well-maintained lawn. The front features a welcoming entrance, flanked by large windows that provide plenty of natural light. Neatly trimmed bushes and trees surround the property, enhancing its appeal.

4.83 out of 5 average rating, 18 reviews

LOCATION! Sea Captain's House, Walk to Beach/Town

A spacious living area is illuminated by natural light from large windows. Comfortable seating options, including a sectional sofa and armchair, surround a coffee table. A dining area with a wooden table is visible, complemented by a staircase leading to the second floor.

4.94 out of 5 average rating, 34 reviews

Chatham Family Vacation

The exterior of the coastal retreat features a welcoming entrance with a brick pathway leading to a charming blue door. Lush green grass surrounds the home, adorned with vibrant hydrangea bushes in shades of blue and lilac on either side.

5 out of 5 average rating, 87 reviews

Lovely Cape Cottage Home < 1 mile to the beach!

The cottage features a welcoming entrance framed by a stone staircase leading to a well-maintained front yard. Lush greenery surrounds the home, with a vibrant garden by the path and a flag gently waving by the door. Clear skies create a bright atmosphere.

4.86 out of 5 average rating, 35 reviews

Chatham Cottage- Close to Downtown & Beaches

Private house rentals

A spacious deck is bordered by lush greenery and tall trees, offering a view of the surrounding landscape. A large, light-colored wooden table is accompanied by several matching chairs, creating an inviting outdoor dining area. Natural light illuminates the scene under a clear blue sky.

4.77 out of 5 average rating, 47 reviews

Ocean View-Semi-Private beach-Jacuzzi-3 BR-AC

4.85 out of 5 average rating, 13 reviews

An outdoor dining area is positioned on a wooden deck, featuring a large dark green table surrounded by matching chairs. The view overlooks a sandy beach and calm ocean waters under a clear blue sky, providing a serene setting for meals.

Home in Sandwich

Beachfront Beauty

The cottage is nestled among trees, displaying a classic shingle exterior. A welcoming screened-in porch with multiple windows provides natural light. The landscaped yard features greenery and flower beds, along with a set of wooden steps leading up to the home.

4.96 out of 5 average rating, 49 reviews

Chatham Beach Cottage 2BR - 5 min walk to beach

4.95 out of 5 average rating, 62 reviews

In-Town Newly Renovated Cape with Central AC

The exterior of the cottage is framed by a lush green lawn and manicured shrubbery. A welcoming pink door serves as the focal point. Shade is provided by a large tree in the foreground, enhancing the serene atmosphere of the setting.

5 out of 5 average rating, 86 reviews

Charming Chatham Home! Less than Mile To Beach !

4.99 out of 5 average rating, 67 reviews

Thinking of Summer Already? - Book Now Summer '26

A charming cottage is framed by tall white pine trees, providing shade and privacy. The exterior features light-colored siding and blue shutters. Seating options include two outdoor chairs positioned on the ground amidst pine needles. A screened-in porch is visible on the right side of the building.

4.88 out of 5 average rating, 41 reviews

Chatham cottage w/ laundry & AC! Walk to beach!