House holiday rentals in Chatham

4.98 out of 5 average rating, 112 reviews

A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.

Home in Harwich Port

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Sun filled open concept living room with a large kitchen island. Great for families ! Less than 4 min drive to Red River beach and Bank street Beach. 3 min drive to Wychmere Beach Club wedding venue. Close to Harwich Port downtown. Centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy a hike to Harwich Thompson's field Conservation area. Close to bike trail

4.83 out of 5 average rating, 197 reviews

The exterior of The Drake Cottage is surrounded by lush greenery and a well-landscaped yard. The charming two-story structure features a mix of wood and stone siding, complemented by a gravel driveway leading to the entrance. Natural stones and native plants are arranged in the gardens.

Home in Brewster

The Drake Cottage - Brewster Beach Getaway

Experience quintessential Cape Cod in The Drake Cottage located right on 6A in Brewster, Ma. The Drake Cottage is conveniently situated within a mile of Drummer Boy Park, The Cape Museum of Natural History, Paines Creek Beach and a 9 min drive from Oceans Edge. The cottage offers an expansive private back yard with an acre of land. Enjoy a newly extended patio complete with fire pit, 10 person picnic table and BBQ grill. Our newly updated interior provides our guests with many modern amenities.

5 out of 5 average rating, 184 reviews

An outdoor dining setting features a table with a plate of salad and wine glasses, accompanied by a bottle of white wine. In the background, a charming shed displays ‘Cape Away’ signage, surrounded by well-maintained greenery and a cozy lounge area.

Home in South Yarmouth

Cozy King Beds w/ Sauna, Bar, Neflix, Hulu, ESPN

Cape Away is a cozy, and entertainment focused family & pet friendly retreat in the charming Mid-Cape region. Start your mornings with coffee in the fully stocked kitchen, hit up nearby beaches, then unwind in the sauna, outdoor shower, or by the fire. With games, private fenced backyard, shed bar and fast WiFi, you’re 5–10 minutes from top restaurants and beaches. We included unlimited Disney+, Hulu, ESPN, Netflix and PrimeVideo for all guests! Book now and make your Cape Cod memories here.

4.93 out of 5 average rating, 113 reviews

A spacious outdoor area features a circular arrangement of colorful chairs, including blue, red, and green options. The inviting lawn is framed by trees, with a large glassed-in porch visible in the background, providing a seamless connection to the natural surroundings.

Home in Harwich Port

Stunning Home in Harwich Port

Welcome to our stunning retreat in charming Harwich Port! This beautiful 4-bed, 2-bath home is the perfect destination for your next getaway. The spacious interior and finished basement are perfect for families or groups and the big fenced-in yard is ideal for outdoor activities, relaxation and pets (please include pets when booking)! A 5 min drive from the beach and downtown, you'll enjoy all that the area has to offer. Book today and experience the best of Cape Cod in this beautiful home!

5 out of 5 average rating, 291 reviews

The exterior of a classic Cape Cod home is framed by a grassy yard under a partly cloudy sky. White wooden adirondack chairs sit on the lawn, and the house features a cozy front porch, shutters in a deep hue, and multiple windows allowing natural light.

Home in West Yarmouth

The Pearl: 3 Bedroom 500 steps to Englewood Beach!

The Pearl is a classic Cape Cod 3-bed home 500 steps to Lewis Bay. Walk through the marsh path on your way to Englewood Beach, a number of small beaches, & Colonial Acres! Seagull Beach is 2 miles away. • Mesh WiFi, 2 Smart TVs • Central Air Conditioning • Large 2nd-floor bedroom • Big yard on a quiet dead-end street • Original wood floors/trim • Living/Dining rooms • Outdoor shower, grill, deck, firepit • Equipped kitchen • Linens/towels provided • Washer/Dryer in basement • Work from home

5 out of 5 average rating, 223 reviews

A quaint historic home features classic shingle siding and a welcoming green front door. Windows with evenly spaced panes provide a glimpse of the interior, while a white picket fence and lush greenery frame the property, creating an inviting setting.

Home in Sandwich

Quintessential Waterfront Historic Cottage

Set in a historic district and on a quiet pond shore, create memories with family and friends that will last a lifetime. Enjoy quintessential New England views from every angle. Coffee, restaurants, shopping & a fresh spring water fountain within a short walk to village center and under a mile to the nearest beach. Spend time walking the local area, exploring Cape Cod and relaxing in an atmospheric setting. Each room has been curated in a timeless tone, with relaxation and comfort in mind.

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, 298 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, 101 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 bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.

4.97 out of 5 average rating, 157 reviews

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

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.

4.91 out of 5 average rating, 196 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).

4.99 out of 5 average rating, 372 reviews

A serene outdoor seating area is set by the waterfront, featuring two chairs with teal cushions and a white table. Lush greenery surrounds the area, enhancing the view of the calm waters and trees beyond. Lanterns add a subtle decorative touch to the space.

Home in Yarmouth Port

Fabulous Waterfront with Spectacular Sunset Views!

**Waterfront on salt water Follins Bay which is the headwaters of the Bass River. Sit and watch the boat activity from the deck or patio. Swim, fish or kayak (2 provided) right from your the backyard on your own private dock. Bright & airy décor with beautiful water views.

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, 188 reviews

Close to everything in Chatham

4 bedrooms ( 1 King bed, 3 Queen beds, 2 Twin beds and a Queen sofa sleeper), 2 1/2 baths, sleeps 10, 3 levels of living space, yard and patio, deck bbq, lounge chairs, large patio table with umbrella, outdoor shower and washer and dryer.

Popular amenities for house rentals in Chatham

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

A private outdoor pool area is enclosed by a white fence and surrounded by greenery. The inviting blue water is complemented by sun loungers, an umbrella, and Adirondack chairs positioned for relaxation. The pool area features a spacious patio for sunbathing and outdoor enjoyment.

Home in North Eastham

Heated Pool, Game Room, Projector Room, Private

5 out of 5 average rating, 33 reviews

An aerial view showcases a tranquil swimming pool surrounded by a spacious lawn. Adjacent seating areas, including sun loungers and a fire pit with chairs, are positioned within the private fenced yard. Lush greenery and garden beds enhance the outdoor space.

Home in Harwich Center

Harwich Haven: Pool & Fire Pit

Superhost

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

4.76 out of 5 average rating, 33 reviews

Heated Pool Oasis | 5 Min to Cape Cod Beaches!

4.9 out of 5 average rating, 20 reviews

A sunny outdoor area is showcased, featuring a private heated pool surrounded by lounge chairs. Large blue umbrellas provide shade next to the pool, while decorative landscaping and a wooden playset are visible in the background. The space invites relaxation and comfort.

Home in Harwich

Cape Cod Heated Pool Putt-Putt Golf Speak Easy Gam

A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.

5 out of 5 average rating, 9 reviews

Heated Pool. Hot Tub. Game Room. Beach Nearby!

4.93 out of 5 average rating, 209 reviews

The exterior of a charming house is shown, featuring a gray shingle facade and a welcoming covered porch. Lush greenery and ornamental shrubs frame the entrance, while a gravel driveway leads up to the front door, creating an inviting approach.

Home in Oak Bluffs

Spectacular beach & pool combo; beautiful sunsets!

4.9 out of 5 average rating, 306 reviews

A view overlooking a well-maintained pool surrounded by green grass, with beach access visible in the distance. The landscape features a mix of trees and charming houses, set against a clear blue sky and tranquil water.

Home in Plymouth

Ocean Side, Amazing View, close to town/beach, Spa

4.9 out of 5 average rating, 147 reviews

A heated indoor pool is framed by sleek gray walls and illuminated with recessed lighting. Large sliding glass doors offer a view of the outdoor patio. Colorful pool floats and equipment are neatly arranged nearby, providing options for leisure activities.

Home in Plymouth

Seaview Summit | Ocean Views, Indoor Pool, Beach

Weekly house rentals

A charming two-story cottage is presented, featuring a shingled exterior and accented by blue shutters. An American flag hangs proudly by the front door, surrounded by greenery and a white picket fence. The inviting pathway leads to the entrance, emphasizing the home's outdoor appeal.

5 out of 5 average rating, 41 reviews

Charming Chatham Cottage - 5 MIN Walk to the Beach

A bright living area features a blue sectional sofa and a colorful coffee table with intricate designs. In the background, an open kitchen is visible with modern appliances and bar seating. Natural light enhances the spacious feel, complemented by light hardwood flooring.

5 out of 5 average rating, 84 reviews

Chatham: Tennis, water views/access, pet friendly!

A calm freshwater pond is surrounded by lush greenery and tall trees. A float is visible on the water, providing a serene spot for relaxation. Lilypads are scattered across the surface, reflecting the clear blue sky.

4.92 out of 5 average rating, 95 reviews

Spacious studio on lovely pond in Chatham

Superhost

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.

4.87 out of 5 average rating, 15 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, 31 reviews

Chatham Family Vacation

An aerial view showcases a serene landscape with a freshwater pond surrounded by lush greenery. A residential neighborhood is visible in the background, along with a clear path leading to the house. The natural environment complements the peaceful setting of the Chatham area.

4.97 out of 5 average rating, 30 reviews

Central AC, Pet-friendly, Walk to water & town!

An aerial view captures the layout of the property, featuring two houses connected by a spacious driveway. Lush greenery surrounds the homes, with blooming azaleas in vibrant colors near the entrance. The backyard is expansive and well-maintained, providing a sense of seclusion.

4.96 out of 5 average rating, 70 reviews

2 House Compound, Huge Yard, Game Room, Kayaks

4.98 out of 5 average rating, 94 reviews

The exterior of the Brewster Farmhouse is showcased, featuring a charming stone facade with green trim. A well-maintained yard surrounds the house, adorned with autumn foliage. The entryway includes two large windows framed by shrubs, with a welcoming double door at the center.

Home in Brewster

Cape Cod Farmhouse: Walk to the Beach in Brewster!

Private house rentals

4.96 out of 5 average rating, 68 reviews

An outdoor seating area is presented with plush, striped furniture and a large firepit at the center. A bright turquoise umbrella provides shade, while the tranquil waterfront view showcases shimmering water and greenery. Potted flowers add a touch of color to the serene setting.

Home in Harwich

Waterfront★ Pvt Beach ★ On Bike Path ★Bikes★Kayaks

5 out of 5 average rating, 24 reviews

A charming single-story home is framed by lush green lawns and minimal landscaping. The exterior features shingled siding and a welcoming front porch. Large windows and a set of double doors provide natural light. A gravel driveway leads up to the entrance, surrounded by trees.

Home in Harwich Port

Your beach home away from home!

The exterior of a recently renovated house is shown, featuring blue siding and white trim. Two symmetrical green shrubs accompany the entrance, which has a red door adorned with a decorative wreath. Windows with red shutters provide a balanced look to the facade.

4.98 out of 5 average rating, 43 reviews

Chatham House Close to Beaches and Bike Path.

5 out of 5 average rating, 30 reviews

Home in Brewster

Newly remodeled cottage with path to beach

5 out of 5 average rating, 94 reviews

Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

5 out of 5 average rating, 71 reviews

A charming ranch-style home is presented, surrounded by a spacious green lawn and meticulously landscaped flower beds. A stone-lined path leads to the entrance, where vibrant orange flowers add a touch of color. The exterior features a combination of siding and a brick chimney.

Home in Harwich Center

* Top Rated - Free Cleaning & Linens - SuperHost!

4.95 out of 5 average rating, 78 reviews

A cozy exterior view of the home features a gravel yard illuminated by string lights, creating a warm ambiance. A fire pit surrounded by log seats invites relaxation. A small patio area with white chairs is visible, along with the welcoming entrance lit by the evening glow.

Home in Hyannis

The Corner Place

A sun-filled living room features large windows allowing natural light to illuminate the space. Two rocking chairs are positioned beside a comfortable sofa. A wooden coffee table sits at the center, with a media console and wall-mounted TV offering entertainment options.