Chatham beach 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.

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.

4.99 out of 5 average rating, 240 reviews

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

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.

4.94 out of 5 average rating, 185 reviews

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 !

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.

4.99 out of 5 average rating, 120 reviews

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.

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.

4.95 out of 5 average rating, 170 reviews

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

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**

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.

4.86 out of 5 average rating, 103 reviews

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.

A textured starfish design in shades of blue is featured on a white wooden fence, adding a coastal touch to the surrounding area. The backdrop includes green foliage, enhancing the serene atmosphere.

4.9 out of 5 average rating, 147 reviews

Forbes, a South Chatham cottage

This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only !

Vacation rentals for every style

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Popular amenities for Chatham vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Chatham vacation rentals

An outdoor deck is presented, featuring a stainless steel grill and seating area with comfortable outdoor furniture. Surrounding trees provide shade, and bright blue skies create a cheerful atmosphere. The deck offers a welcoming space for relaxing or entertaining.

4.95 out of 5 average rating, 63 reviews

2 bedroom apartment

4.93 out of 5 average rating, 41 reviews

Chatham Beach Cottage 2BR + Loft Walk to the Beach

A historic lighthouse stands tall beside a charming white building, framed by neatly trimmed hedges. Lush green trees and vibrant blue skies create a serene backdrop, enhancing the coastal landscape. The lighthouse’s watchtower is adorned with windows, completing this scenic view.

4.67 out of 5 average rating, 21 reviews

Cozy Chatham Cape Cod Cottage

5 out of 5 average rating, 18 reviews

Home in Brewster

Newly remodeled cottage with path to beach

A back deck features modern outdoor furniture, including a sectional sofa with navy cushions and a light-colored coffee table. Lush greenery surrounds the space, offering a serene atmosphere. The outdoor shower is visible in the corner, providing convenience after beach activities.

4.98 out of 5 average rating, 82 reviews

Beachfront Charmer! Newly Renovated.

An open kitchen area features a light grey wall with a decorative anchor motif. A clean countertop is seen with modern appliances, including a microwave and coffee maker. Two sturdy bar stools with grey cushions provide seating at a quartz bar, complemented by a colorful area rug.

4.92 out of 5 average rating, 53 reviews

Chatham Condo with private entrance

A welcoming living area displays a rustic coffee table with neatly stacked, crisp white towels featuring blue stripes. Light streams through large windows, illuminating a light sofa adorned with blue cushions. A striped area rug adds texture to the hardwood flooring.

4.87 out of 5 average rating, 62 reviews

Updated 4BR Home, close to Beach, Town & Bike Path

A serene beach scene displays soft, sandy dunes adorned with tufts of tall grass, gently swaying in the breeze. The calm ocean stretches into the distance under a cloudy sky, offering a tranquil natural setting.

4.99 out of 5 average rating, 71 reviews

Serene Chatham cottage minutes from beach

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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

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.

4.95 out of 5 average rating, 58 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

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, 18 reviews

Red Door Retreat in Chatham is 80% full for summer

4.88 out of 5 average rating, 90 reviews

Walk to beach! Chatham Luxury near downtown, CBI!

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

A spacious deck is visible, surrounded by lush greenery and tall trees. A large umbrella shades a seating area, which includes outdoor furniture. Bright flowers are planted along the deck's edge, enhancing the inviting outdoor space.

4.97 out of 5 average rating, 103 reviews

Chatham Charm

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

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.