House vacation rentals in Chatham

The exterior of a charming Cape Cod cottage features a light grey wood siding and traditional doghouse dormers. A white picket fence encloses a landscaped yard, with rocking chairs positioned on the front patio, offering views of the surrounding area.

5 out of 5 average rating, 23 reviews

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front brick patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage, complete with original quarterboard outside and traditional doghouse dormers on the 2nd floor. Chatham Seaside Links located across the street. Clubs and carts available for rental at the course. Private driveway with off street parking. Wonderful views of the harbor from the front brick patio. Charm and warmth of an original quaint Cape Cod Cottage with traditional doghouse dormers on the second floor. Walk to town location with summer concerts at the end of 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. On 12/28/18, the State of Massachusetts enacted new tax legislation impacting any vacation rentals of 90 days or less. All reservations for stays commencing 7/1/19 forward will be subject to State and Local occupancy taxes. These taxes will be reflected in the lease agreement you will receive following the receipt of your initial reservation request. AirBnB is unable to reflect any taxes with future effective dates within the pricing calendar of their website and have requested property owners to manage the collection process of these taxes separately until this feature is enabled in a future version of their website or the actual effective date of the tax, whichever is earlier.

Superhost

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.

4.89 out of 5 average rating, 133 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 home away from home vacation house are linens, towels, fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, & 4 season porch to relax on.

5 out of 5 average rating, 165 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 Yarmouth

Entertain and Relax | King Beds * Sauna * Bar Shed

Welcome to Cape Away, your charming family & pet-friendly retreat! Enjoy a fully stocked kitchen, cozy fireplaces, sauna, and outdoor shower. Unwind with dozens of board games, dart board, fire pit, and BBQ. The fully fenced private backyard offers beach gear, a bar shed and lounge area. We are perfectly located just 5–20 minutes from top rated restaurants and beaches, making it your ideal home base. With premium amenities, thoughtful touches it’s the perfect space to escape, explore and relax.

Superhost

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

Home in Brewster

4.87 out of 5 average rating, 215 reviews

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

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, 291 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 gravel driveway leads up to a charming two-bedroom home surrounded by lush greenery. A white picket fence outlines manicured garden beds, while a spacious front porch is visible through large windows, allowing for natural light to enter the inviting living space.

4.95 out of 5 average rating, 38 reviews

2 BR w A/C, near beach, Main St., CBI, Wequossett

Welcome to our delightful 2 BR 1 BA home, a mile to the beach and CBI, 1.2 miles to Main Street, .5 mile to the bike path, and 3 miles to Wequosset. This dog-friendly retreat perfectly combines peace and accessibility, making it an ideal destination for your vacation in the picturesque Chatham. Inside, you'll find a bright and welcoming ambiance, complete with tasteful decor & furnishings. An expansive outdoor space features a fully fenced-in yard, perfect for outdoor games and activities

Superhost

A modern kitchen features white cabinetry and stainless steel appliances. A large island with seating for two is positioned next to a dining table with light wood chairs. Natural light fills the space through sliding glass doors leading to the outdoor area.

4.96 out of 5 average rating, 106 reviews

Chatham Charm

Welcome to our newly renovated 4-bed, 2-bath Cape house close to downtown Chatham and beaches! The house is equipped with central air, wifi, a living room TV with cable, smart TVs in bedrooms, and a washer/dryer set. The property also includes a large deck and back yard, great for grilling and outdoor activities. We have a contractor nearby to help with any needs you may have during your stay. Sat-Sat 7-night minimum stay last 2 weeks of June through end of August.

4.98 out of 5 average rating, 197 reviews

An inviting living area features a comfortable seating arrangement with a grey sofa and an accent chair. A dining table is visible, accompanied by floral arrangements. Warm light filters through large windows, illuminating the space, while a fireplace and decorative elements enhance the cozy atmosphere.

Home in Brewster

SeaPeace Cottage-East Brewster Deck,Firepit,W/D AC

• Fully equipped + stocked kitchen • Driveway parking for 3 vehicle + boat • Outdoor fire pit + hammock • Enclosed outdoor hot shower + sink • Access to private Blueberry Pond • Private deck Weber gas grill Cape Cod corn Hole yard game • Onsite washer + dryer • 15min drive to Chatham • 10min drive to Orleans Stroll to Nickerson State Park 6 Adirondack chairs Sea Peace Cottage-East Brewster

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, 90 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

4.96 out of 5 average rating, 110 reviews

A charming living room features a comfortable sofa with blue and white patterns, situated beside a warm gas fireplace. Sunlight filters through windows, illuminating a coffee table with a tray and snacks. Bookshelves adorned with decorative items line the walls, enhancing the cozy ambiance.

Home in Harwich Port

Pebbles-romantic cottage for two!

Pebbles, our sun drenched romantic cottage, is on nearly an acre of complete privacy with convenient parking. One adorable king BR, queen pull-out sleeper sofa in the living room, gas fireplace heats entire cottage, cable TV, full internet. Full indoor bath and outside shower and tub--complete privacy. Full kitchen and eating area.

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, 189 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).