Chatham vacation rentals

4.99 out of 5 average rating, 240 reviews

A clean bathroom is equipped with a modern white toilet and a sleek vanity. Decorative framed shell prints adorn the wall above, while a countertop holds various bottles and a hand soap dispenser. Natural light streams in, adding a bright touch to the neutral tones.

Guest suite in Chatham

Waterfront Suite on Emery Pond

Comfortably furnished studio suite w/private parking & entrance offers a garden setting w/picnic table just steps to a fresh water pond & outdoor shower. The friendly, cottage-style decor is inviting w/queen-size bed, couch, ample closets, private bathroom w/shower, small dining area w/microwave & fridge (no stove, no bbq); writing table, WiFi, Roku & DVD player. Enjoy the water view! Minutes by car to downtown Chatham. Fresh linens, bath & beach towels, shampoo/conditioner, coffee/tea. STR-46

4.94 out of 5 average rating, 187 reviews

A historic black-and-white photograph captures the exterior of the Captain Kimball House. The two-story building features colonial-style shutters and a sloped roof. A white picket fence encloses the property, with a tree and individuals seated in front, reflecting a sense of the past.

Guest suite in Chatham

The Captain Kimball House of Christmas Joy

Experience Cape Cod while staying in this historic 1735 Salt Box built by Captain Kimball Eldredge. You will have a private entrance and the entire second floor dwelling to yourself. Conveniently located on 28 with just a short walk to the beach, this recently renovated home showcases colonial craftsmanship with the original wood floors and fireplaces. Two restaurants a stones throw away, the Cape Cod Rail Trail down the street and only a five minute drive to downtown Chatham or Harwich Port.

The modern kitchen features a spacious white sink and granite countertops, complemented by a sleek stove and stainless-steel appliances. Natural light floods the space through large windows, offering scenic views of the surrounding landscape. Open shelves display tableware, enhancing the contemporary design.

4.95 out of 5 average rating, 279 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.

4.99 out of 5 average rating, 120 reviews

Several boats are anchored in a calm waterway, displaying a variety of colours, including orange and turquoise. The sky above features soft clouds and a gentle gradient from blue to pink, creating a serene backdrop for the scene.

Guest suite in Chatham

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

Guest suite in East Harwich

A spacious backyard features a well-maintained lawn, surrounded by lush greenery. A wooden deck with seating overlooks the area, complemented by colorful flower pots. A hammock is nestled between trees, inviting relaxation. Comfortable chairs are arranged for outdoor enjoyment.

4.99 out of 5 average rating, 605 reviews

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

4.97 out of 5 average rating, 264 reviews

An exterior view of a two-story wooden home surrounded by lush greenery and landscaping. A spacious deck with a green umbrella leads to the entrance, while large stone accents border the grassy yard. The natural setting offers a sense of privacy.

Apartment in Chatham

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

4.88 out of 5 average rating, 91 reviews

Condo in Chatham

Walk to beach! Chatham Luxury near downtown, CBI!

Chatham Searenity! BEACH ACCESS! Walk to beautiful beach overlooking monomoy! 2 minutes from Chatham Bars Inn, Chatham links golf & downtown! Luxury 2 bedroom, 2 bath condo with full kitchen & cookware. Quiet, comfy space centrally located. Peaceful, relaxing private space with large queen bed, daybed w/ pull out trundle, A/C, washer dryer, Wifi & ample parking. Hulu live tv, Netflix, Prime video, HBO max, Disney+. Central to everything! Perfect Cape escape. IG @chatham_searenity

4.94 out of 5 average rating, 173 reviews

A cozy cottage is framed by tall trees, showcasing a landscaped yard with a mix of grass and small shrubs. The home features a light-colored exterior with dark shutters and a welcoming front porch with steps leading up to the entrance.

Cottage in Chatham

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

5 out of 5 average rating, 48 reviews

The exterior of the building is showcased, featuring a modern wall lantern mounted beside the entrance. The house number '757' is displayed in sleek typography, enhancing the welcoming facade. The entrance door, painted in a soft blue color, complements the neutral siding.

Vacation home in Chatham

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

4.96 out of 5 average rating, 332 reviews

Condo in Chatham

In-town, Pied-a-Terre. Private, Sunny Urban Oasis

Bright, Sunny, great in-town location. CLEAN, SAFE & PRIVATE and spacious, hidden ABOVE shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Full Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

4.86 out of 5 average rating, 103 reviews

A serene pathway leads to a row of inviting patio chairs positioned under an overhang. Large windows line the front, offering clear views of the beachfront. Lush green grass and neatly trimmed landscaping enhance the peaceful outdoor setting.

Condo in Chatham

Steps to Private Beach in Chatham

2 Bedroom condo with views of the beach, ocean and marina. This wonderful condo is part of a beachfront/oceanfront complex, with steps to your own private beach in Chatham! We are within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous lighthouse beach and Monomoy Wildlife refuge. Whether by land or sea, there's something for everyone. This is a great place to make memories.

Three textured starfish decorations are mounted on a white wall above a wooden headboard. The headboard supports a bed decorated with patterned pillows, enhancing a coastal theme.

4.91 out of 5 average rating, 186 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).

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Chatham vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Chatham

Superhost

A spacious outdoor seating area is arranged around a sleek fire pit, featuring an array of blue glass stones, with flames dancing atop. Comfortable, neutral-toned cushions adorn the sectional seating, complementing the natural greenery visible in the background under a clear blue sky.

4.95 out of 5 average rating, 21 reviews

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

4.94 out of 5 average rating, 47 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

4.95 out of 5 average rating, 59 reviews

A vibrant blue door is open, revealing a picturesque view of grassy areas leading to a body of water. Soft sunlight streams in, highlighting the inviting space. Outside, white Adirondack chairs are visible, positioned on the lawn to enjoy the scenic view.

Cottage in Chatham

Renovated Chatham Windmill! Walk to Beach/Town!

A charming cottage featuring a light shingle exterior and a welcoming front porch, surrounded by lush greenery. Comfortable seating is provided in the foreground, with colorful flowers adding a vibrant touch to the serene setting. The driveway is lined with smooth stones leading to the entrance.

4.97 out of 5 average rating, 29 reviews

Chatham Beach Cottage 2BR - 5 min walk to beach

A welcoming porch is shown, adorned with white railings and flower beds featuring hydrangeas and lavender. The entrance leads into a serene landscape with green grass and trees, capturing the essence of a peaceful outdoor space.

5 out of 5 average rating, 19 reviews

Red Door Retreat in Chatham is 80% full for summer

5 out of 5 average rating, 9 reviews

Luxury Home- Chatham Center- Walk to Town + Beach

Superhost

A sandy beach scene is presented with gentle curves leading to a serene body of water. Dune grass and scattered shrubs provide natural textures in the foreground, while an expansive blue sky stretches above. The scene captures the tranquil beauty of the coastal environment.

Apartment in Chatham

4.83 out of 5 average rating, 18 reviews

Bright Condo on private beach

A serene beach scene is presented with soft sand in the foreground and calm water extending towards the horizon. Several boats gently float on the water under a clear blue sky, showcasing a peaceful coastal atmosphere.