Chatham vacation rentals

A serene coastal view features several boats gently bobbing on calm waters. The reflective surface of the water showcases a palette of blues and greens, with a soft, overcast sky in the background, conveying a tranquil atmosphere.

4.89 out of 5 average rating, 130 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.

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, 185 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.

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.

4.97 out of 5 average rating, 373 reviews

A vibrant sunset is displayed over a tranquil beach, featuring rich hues of orange, pink, and purple across the sky. Gentle waves lap at the shore, reflecting the warm colors of the sunset. The horizon meets the water, creating a serene atmosphere.

Guest suite in Brewster

Sheep Pond Get-Away

The AirbNB Studio Space is Private w/ its own separate entrance & exit. Our home is set in the 'Sheep Pond' area. We are walking distance to Sheep Pond to kayak & swim. We have kayaks, paddleboards, beachchairs, & towels for your use. A backyard w/ your own picnic table, seating area, & hammock. An outdoor shower ! Minutes away from bay & oceanside beaches, biking, hiking & Nickerson State Park. 40 mins from Provincetown; & surrounded by quaint Route 6a, restaurants & shopping !

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, 604 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, 263 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.

4.95 out of 5 average rating, 170 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.

4.96 out of 5 average rating, 330 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, 185 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

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Quaint homes, peaceful surroundings

Popular amenities for Chatham vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Chatham

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, 20 reviews

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

LakshmikantRating, 5 stars2 weeks ago

We had a great stay - the weather was uncooperative, but having such a beautiful house really helped. The pool and hot tub were great, as was the built-in grill. There was plenty of space for everyone and having 4 bathrooms was great when everyone was getting ready.

5 out of 5 average rating, 34 reviews

A serene beach scene showcases a gently curving sandy shoreline meeting calm waters. Several charming houses are positioned along the coast, framed by lush greenery and rocks, under a sky filled with soft clouds and blue hues.

Cottage in Chatham

"Escape Hatch' Chatham, In town Location

ConstanceRating, 5 stars8 months ago

Lovely cottage on a quiet street. Great location for walking into town and to several beaches. Nicely arranged backyard with comfortable chairs and dining table. And Ahhh the sun drenched outdoor shower was such a treat. I’d highly recommend this little gem.

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!

eileenRating, 5 stars2 weeks ago

Absolutely sparkling fresh and clean. Beautifully designed and decorated. Bed was so cozy and comfortable. Stairs are tricky and steep But it is expected in this style cottage. Convenient to downtown yet very secluded. We had a nor easter through our visit. So sad that our outdoor plans were ruined but this cottage had lots of room to move around. Could not imagine being in a small hotel room. We loved handing out at Chatham Bars Sacred Cod for drinks and dinner! Coming home to our cottage was half the hotel price but twice as cool!

4.88 out of 5 average rating, 90 reviews

Condo in Chatham

Walk to beach! Chatham Luxury near downtown, CBI!

KathyRating, 5 stars3 weeks ago

Kathryn place was just as advertised. Was a lovely unit and easy to explore Chatham in the surrounding areas. Katherine provided clear check in instructions and followed up promptly with any questions we had. I would definitely recommend staying here.

A spacious living area features a brown leather sectional and two white armchairs, creating a cozy seating arrangement. Natural light floods in through large windows, illuminating the wooden flooring. An elegant chandelier hangs above a coffee table in the center, providing a welcoming ambiance.

5 out of 5 average rating, 9 reviews

Luxury Home- Chatham Center- Walk to Town + Beach

AnjuRating, 5 stars8 months ago

This place was excellent . Very clean and beautiful. Walkable to many restaurants n shopping locations. Prompt communication from the host. Would be happy to stay here any time again.

4.83 out of 5 average rating, 18 reviews

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

Bright Condo on private beach

SuzieRating, 5 stars3 weeks ago

Loved the location! There were people nearby but it was quiet. Great access to walk on the sand by the water. Inside, the bed was comfortable and I found everything I needed for the one dinner I ate in. I enjoyed sitting out on the patio in the back as well. Would love to stay again.

A calm freshwater pond is surrounded by lush trees, reflecting the sky in the clear water. A vibrant red float is seen anchored in the center, providing a tranquil spot for relaxation. The shoreline features greenery, enhancing the peaceful atmosphere.

4.91 out of 5 average rating, 86 reviews

Spacious studio on lovely pond in Chatham

EmilyRating, 5 stars2 days ago

Thanks for being a warm, friendly, and welcoming host Ragnhild! Enjoyed staying in this peaceful guest suite with a water view. The WiFi is also very fast, and I was able to seamlessly video conference on Teams. Would recommend Ragnhild’s place to any potential guests, especially remote workers.

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.