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, 52 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, 13 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 cozy sleeping area features a spacious bed with a light coverlet and two accent pillows. Artwork in various frames adorns the wall above, complemented by wall-mounted sconces. A small bedside table holds books and a decorative plant, enhancing the room's inviting ambiance.

5 out of 5 average rating, 8 reviews

New! Chatham Cozy Cottage on White Pond

Petite & sweet 2 room 1920s cottage in convenient location. Shared waterfront access steps away. Updated to include all essential modern comforts while maintaining its historic charm. Every detail is considered to maximize the space’s function within a small footprint. Quiet ductless A/C and heat will keep you cozy. New bathroom with shower. Queen bed. Front deck with grill and seating. Includes 1 parking spot. Linens and Bath Towels included, please bring your own beach towels and chairs.

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.

4.96 out of 5 average rating, 312 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 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.

4.97 out of 5 average rating, 31 reviews

Close to Beach Renovated Dog Friendly Cape Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

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.

4.97 out of 5 average rating, 115 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, 172 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.

Superhost

A charming cottage exterior is showcased, featuring natural wood siding and flower boxes below the windows. The entrance is framed by shrubs, while a grassy area surrounds the cottage. Mature trees provide shade, enhancing the peaceful setting in a tree-filled neighborhood.

4.84 out of 5 average rating, 159 reviews

Delightful Chatham Cottage, Cheerful and Clean

AirBnB Superhost, local owner has 25 years of online vacation rental experience with this property. Refreshed and updated , our 1 bedroom cottage is an ideal getaway spot for a couple or young family. The cottage is located on a 1/2 acre lot in the geographical center of Chatham, on a private road in a quiet, tree-filled neighborhood. Guests all agree that we have a fantastic location at an affordable price. Enjoy a relaxing stay while being close to everything in town.

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, 101 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.

A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.

5 out of 5 average rating, 29 reviews

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

A spacious living room features a comfortable blue sectional sofa and a white armchair, arranged around a wooden coffee table. A modern floor lamp provides soft lighting. A fireplace is flanked by built-in shelves displaying books and decor, with large windows allowing natural light to fill the space.

5 out of 5 average rating, 13 reviews

Walkable to Downtown Chatham Home with Bikes

Escape to The Nook on Nob Hill, a stylish 3BR/1BA Cape Cod getaway in Chatham for 6. Just a 5-min walk to downtown and steps from the Cape Cod Rail Trail. Enjoy modern coastal charm, a fully equipped kitchen, a fire pit, and family-friendly amenities. Perfect for families and outdoor lovers seeking a convenient and comfortable base to explore the Cape. Recently named a top Fall stay by Capeology!

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, 102 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

Popular amenities for Chatham house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 17 reviews

A charming single-story home is presented with a neatly manicured lawn, adorned with blooming blue hydrangeas. A flag is displayed on the front porch, and large windows provide a view of the inviting interior. The clear blue sky complements the home's fresh appearance.

Home in Hyannis Port

Renovated Cape Oasis W/ New Pool and Game Room!

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

4.79 out of 5 average rating, 38 reviews

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

4.9 out of 5 average rating, 21 reviews

Home in Eastham

Beautiful Spacious Family Retreat w/ Pool!

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

4 BD slice of Harwich Heaven

4.91 out of 5 average rating, 162 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

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, 131 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

Home in Barnstable County

A bright dining area is illuminated by natural light from large windows, offering views of the waterfront. A small table is surrounded by four blue stools, while a vase of flowers adds a touch of color. A comfortable gray sofa is positioned nearby.

4.89 out of 5 average rating, 27 reviews

Waterfront Bass River Jolly Captain

Weekly house rentals

5 out of 5 average rating, 6 reviews

Home in Eastham

10 min walk to Beach - Amazing View & Huge Deck

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, 46 reviews

Chatham House Close to Beaches and Bike Path.

4.95 out of 5 average rating, 62 reviews

In-Town Newly Renovated Cape with Central AC

5 out of 5 average rating, 16 reviews

Meadow + Main

4.98 out of 5 average rating, 42 reviews

Home in Harwich

The Hideaway - Harwich Port Getaway

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.

4.93 out of 5 average rating, 54 reviews

Chatham Beach Cottage

4.88 out of 5 average rating, 24 reviews

Cheerful 2 bedroom home walk to town location.

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.

4.95 out of 5 average rating, 39 reviews

Chatham Family Vacation

Private house rentals

An outdoor fire pit, surrounded by four white Adirondack chairs, sits on a stone patio. Stone landscaping features greenery and flowering plants in the background, providing a serene setting for gatherings. The flames add warmth to the inviting atmosphere.

5 out of 5 average rating, 24 reviews

Beautifully renovated home, outdoor space, pets ok

A charming two-story house is positioned on a well-maintained lawn. The exterior features light siding with navy blue shutters and a welcoming front door. Two blue Adirondack chairs are placed in front, surrounded by neatly trimmed bushes and a gravel pathway leading to the driveway.

4.93 out of 5 average rating, 29 reviews

Amazing Location! Chatham Center, Walk to Beach!

4.91 out of 5 average rating, 96 reviews

Walk to Ridgevale Beach | Chatham Escape

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, 27 reviews

Downtown Chatham Walk to Everything: 4 Bedroom+

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, 92 reviews

Chatham House Near Town and Beach

The charming yellow house is set against a twilight sky, framed by a white fence and lush greenery. Warm light spills from the windows, casting a welcoming glow on the front porch, which features a bright red door, inviting guests to explore the home.

5 out of 5 average rating, 12 reviews

Happy Yellow House, Walk to Ridgevale Beach!

4.85 out of 5 average rating, 13 reviews

Elbow Inn, Private Retreat with 2 Master Suites