House vacation rentals in Chatham

A bright bedroom showcases a spacious bed with white linens and decorative pillows. A wooden dresser and bedside tables are positioned nearby. Nautical-themed decor, including a wall sign and a decorative ship's wheel, enhances the coastal ambiance. Natural light enters through a window overlooking the peaceful surroundings.

4.94 out of 5 average rating, 138 reviews

Walk to Ridgevale Beach

We have done extensive renovation and remodeling to the home with attention to detail. We believe we have created a warm and inviting atomosphere. The home is decorated in a coastal style with carefully chosen accents from the edison bulbs in the dining area to the custom barn/boathouse style door and repurposed hand hewn 18th century beam that anchors the staircase. The Kitchen is equipped with the same attention to detail for those who enjoy preparing their own meals. Summerfell is an entire home rental. Both hosts live nearby, Patty and Bill will be accessible via cell, text and email. The property is in a peaceful neighborhood with a good mix of seasonal homes and full time residences. The area has a number of quiet roads perfect for evening strolls. Of course, the beach is a short 5 minute walk away. The kitchen is equipped for the guest who enjoys cooking. From small appliances (Crockpot, waffle iron, blender, hand mixer etc) to small gadgets (citrus press, microplane, garlic press, potato ricer etc) A three burner weber gas grill is on the deck.

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.

5.0 out of 5 average rating, 103 reviews

Lovely Cape Cottage Home < 1 mile to the beach!

Relax at this charming South Chatham coastal retreat! Situated just 0.8 miles to Forest Beach and close proximity to the Cape Bike Trail -- relax w/ the whole family this summer. Enjoy the extensive outdoor entertaining space that includes a custom fire pit, composite deck, stone patio & Weber gas grille. Walking distance to several restaurants including Bucas, Drifters, Pisces & a short drive or bike ride to Chatham center. Located on a private drive and overlooking acres of conservation land.

The cottage exterior features a light brown facade with white trim, complemented by blooming hydrangeas in shades of blue and purple. A front porch with white railings invites relaxation, while an American flag is displayed. A spacious gravel driveway leads up to the entrance.

4.88 out of 5 average rating, 151 reviews

Cute cottage - walking distance to Ridgevale Beach

Retreat to this very quiet and peaceful residential shore neighbored on a dead end street. If LOCATION is what you're looking for, look no further! This year round cottage will serve as a comfortable and relaxing home away from home for your vacation, with walking rights to Ridgevale Beach about 300 yards from the front door. Provided in your vacation house are linens, towels, a fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, backyard patio & 4 season porch to relax on.

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, 323 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.

5.0 out of 5 average rating, 29 reviews

Meadow + Main

Welcome to Meadow + Main – A Boutique Coastal Retreat in South Chatham Nestled between the peaceful Twine Field Meadows conservation area and South Chatham's Main Street, you'll be just a short walk from the Old Colony Rail Trail while some of Cape Cod's most beautiful beaches, restaurants, golf courses, and villages are only minutes away. The home is notably tucked away from the main road and surrounded by mature trees, creating a peaceful and private setting where you can truly unwind.

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.

5.0 out of 5 average rating, 101 reviews

Charming Chatham Home! Less than Mile To Beach !

Cozy,comfortable and completely renovated this cottage has everything you need for a relaxing stay. Central air, outdoor shower, deck with Weber grill, fire pit, fully stocked kitchen. All linens provided, including beach towels. Less than a mile to Forest Beach and bike path. Short drive to all popular beaches. 10 minutes to Chatham Center, 5 minutes to Harwichport Center. We are nearby should you need anything during your stay , however you have complete privacy. Keyless entry.

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, 120 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!

4.99 out of 5 average rating, 138 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

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

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, 178 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.

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, 106 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.

5.0 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 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, 103 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 free parking

The exterior of a charming beach cottage features weathered cedar shake siding and well-maintained landscaping. A welcoming pathway leads to the entry door, flanked by two sets of windows adorned with flower boxes. The lawn is landscaped with shrubs and mulch.

4.97 out of 5 average rating, 37 reviews

Charming Chatham Cottage

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!

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.

4.96 out of 5 average rating, 51 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.

4.98 out of 5 average rating, 49 reviews

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

5.0 out of 5 average rating, 6 reviews

New! Luxury Home near town, beach, lake access!

5.0 out of 5 average rating, 20 reviews

Dreamcatcher | Luxury Chatham Retreat

5.0 out of 5 average rating, 67 reviews

Charming Cape ~ close to Downtown/Pier/Beach

A well-lit dining and living area features a long wooden dining table surrounded by white chairs. Natural light floods in through large windows, and sliding doors lead to an outdoor deck. A cozy sofa is positioned nearby, creating a welcoming environment.

4.96 out of 5 average rating, 57 reviews

Newly Built Home | 5 Min Walk to Ridgevale Beach

House rentals with a hot tub

4.94 out of 5 average rating, 271 reviews

A waterfront hot tub is set against a natural backdrop of trees and calm waters. Inside, a dining area features a large window with views of the lake. A cozy living room displays comfortable seating, while an outdoor patio has seating for relaxation and enjoying the scenery.

Home in South Yarmouth

Waterfront•Hot Tub • Kayaks/SUP's • King Bed •Dock

4.97 out of 5 average rating, 127 reviews

A covered outdoor seating area features a comfortable sectional sofa with neutral cushions and a round coffee table. A dining table with several chairs is positioned nearby, alongside an outdoor kitchen equipped with a grill. Sunlight casts distinct shadows across the space.

Home in East Falmouth

Seacoast Shores Oasis-Steps From Private Beach Bay

4.9 out of 5 average rating, 332 reviews

A hot tub is situated under a wooden pergola, surrounded by trees reflecting natural greenery. Soft lighting is arranged along the structure, creating a calm ambiance. The tub is partially covered, with jets visible, inviting relaxation after a day at the beach.

Home in West Dennis

Sun Sand & Sea House- Fenced Yard and Hot Tub!

4.96 out of 5 average rating, 240 reviews

A tranquil scene captures a couple seated on a dock, surrounded by tall green grasses. The calm water reflects soft hues of pink and blue from the sunset, creating a serene backdrop of trees across the pond.

Home in Dennis Port

Lakefront House/Private Dock/Year Round Hot Tub/AC

4.98 out of 5 average rating, 172 reviews

The exterior of the house is surrounded by well-maintained greenery and tall, lush trees. A welcoming front entrance is framed by neatly trimmed hedges, leading to a slate pathway and steps. Large windows allow natural light to brighten the façade.

Home in Centerville

Luxury House 0.25 mi from Craigville Beach

4.94 out of 5 average rating, 122 reviews

An outdoor area showcases a gas firepit surrounded by several chairs on a stone patio, under a pergola. In the background, a deck with outdoor furniture and a hot tub is visible, complemented by a fenced yard and lush trees. Sunlight brightens this inviting space.

Home in West Yarmouth

Awesome Cottage near Beach, Backyard Bar & Hot Tub

4.86 out of 5 average rating, 115 reviews

An outdoor space features a cozy seating area with blue cushions surrounding a fire table. A dining table is set nearby, accompanied by a grill and outdoor kitchen. String lights provide subtle illumination, enhancing the space for gatherings. A television is mounted on the wall.

Home in East Dennis

Speakeasy Bar • Hot Tub • PetsOK• Close2Mayflower

5.0 out of 5 average rating, 12 reviews

Home in Dennis Port

Luxury Waterfront - Hot Tub, Deck & Waterviews

Family-friendly house rentals

5.0 out of 5 average rating, 249 reviews

A historic home features classic New England architecture, with a peaked roof and wooden shingle siding. White trim outlines the windows and door, while a white picket fence surrounds the property. Lush greenery and colorful flowers enhance the welcoming exterior under a clear blue sky.

Home in Sandwich

Quintessential Waterfront Historic Cottage

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.

5.0 out of 5 average rating, 29 reviews

Downtown Chatham Walk to Everything: 4 Bedroom+

5.0 out of 5 average rating, 6 reviews

Chatham Home overlooking Cranberry Bog

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.

4.95 out of 5 average rating, 77 reviews

2 House Compound, Huge Yard, Game Room, Kayaks

A charming cottage is seen from the front, featuring natural wood siding and a blue door. Well-maintained shrubs and blooming azaleas accentuate the entrance, while a stone pathway leads to the door, framed by a grassy area and trees in the background.

4.97 out of 5 average rating, 97 reviews

Serene Chatham cottage minutes from beach

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.

4.95 out of 5 average rating, 21 reviews

Walkable to Downtown Chatham Home with Bikes

5.0 out of 5 average rating, 6 reviews

Luxury Chatham Escape w/ Stunning Waterfront Views