Become a host

Vacation rentals in Chatham

Find and book unique accommodations on Airbnb

0 of 0 items showing
1 of 3 pages

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham vacation rentals

Pet friendly
Laptop-friendly workspace
Gym
BBQ grill
Wifi

Chatham beach vacation rentals

Top guest favorite
A sandy beach area is visible, with gentle waves lapping at the shore. A wooden pathway leads down to the water, surrounded by sparse trees and shrubs. The scene is framed by a clear blue sky and distant greenery, creating a serene coastal view.
Cottage in Oak Bluffs
4.94 out of 5 average rating, 153 reviews

Charming water-front cottage on Martha's Vineyard!

Top guest favorite
A view of the waterfront shows a relaxing outdoor seating area featuring a coffee table and comfortable gray sofas. Lush greenery and blooming hydrangeas surround the space, while a clear lake reflects the sky in the background.
Cottage in South Yarmouth
5 out of 5 average rating, 229 reviews

Serenity Views | Waterfront | Kayaks SUP | KingBed

Top guest favorite
The exterior of a quaint cottage is framed by manicured shrubbery and a white picket fence. A welcoming front porch features steps leading to a light blue door, with a house number displayed prominently. Natural surroundings create a serene entrance.
Cottage in Buzzards Bay
5 out of 5 average rating, 210 reviews

140 Steps to Beach with Water Views

Top guest favorite
The exterior of the cottage is surrounded by greenery, with a wooden deck leading up to the entrance. Two adirondack chairs are positioned around a fire pit, while a picnic table and additional seating are visible. A brick chimney adds character to the charming structure.
Cottage in North Truro
4.93 out of 5 average rating, 109 reviews

Unique Waterfront Artist Cottage

Guest favorite
A vibrant green kayak glides over calm waters, with a person seated inside holding a paddle. In the background, a cottage displays large wall-to-wall windows reflecting the surrounding trees, providing a connection to nature.
Cottage in Sandwich
4.95 out of 5 average rating, 239 reviews

WOW LAKE VIEW! Waterfront, Prvt Beach, King Bed!

Top guest favorite
A sandy beach is lined with beachgoers enjoying the sun, and colorful umbrellas provide shade. Gentle waves ripple in the water under a clear blue sky, while grassy dunes frame the scene, highlighting the natural beauty of the coastal location.
Home in North Eastham
4.98 out of 5 average rating, 135 reviews

Private Bay Beach and Sunset Views! Dog friendly.

Guest favorite
A charming cottage is framed by a well-maintained garden, featuring vibrant flowers and lush green grass. The inviting front entrance is highlighted by a pathway leading to a door, with a pitched roof and decorative chimney visible above.
Cottage in Yarmouth Port
4.97 out of 5 average rating, 289 reviews

Amazing Sunkissed Waterfront on Follins Pond!

Top guest favorite
A row of identical beach cottages aligns along the shoreline, with vibrant orange and purple hues of the sunset filling the sky. The cottages sit on stilts, and the gentle waves lap at the sandy beach in front, creating a serene coastal atmosphere.
Cottage in North Truro
4.96 out of 5 average rating, 135 reviews

Daisy of Days Cottages - Cottage on the beach

Pet-friendly vacation rentals in Chatham

Top guest favorite
A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.
Home in West Yarmouth
5 out of 5 average rating, 324 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

Top guest favorite
An outdoor dining area is presented, featuring a rectangular wooden table surrounded by six rattan chairs. A large striped umbrella provides shade. In the background, a mural of an octopus and the words 'Cape Cod' adorns the cottage wall, enhancing the vibrant atmosphere.
Cottage in Yarmouth
4.96 out of 5 average rating, 110 reviews

Charming Cape Cod Getaway near Beaches

Guest favorite
A quaint tiny home is framed by lush greenery, featuring large windows that allow natural light to fill the interior. The exterior includes a spacious deck surrounded by trees and stone pathways, enhancing the connection to nature.
Tiny home in Brewster
4.97 out of 5 average rating, 122 reviews

Waterfront Romantic get away Nest

Top guest favorite
Home in Dennis Port
4.98 out of 5 average rating, 268 reviews

Shirley's Place - Pet Friendly!

Guest favorite
The image captures a dog playing in a shallow stream at sunset. Soft waves ripple through the water, reflecting hues of orange and yellow from the vibrant sky. The landscape features a sandy shore lined with rocks, creating a serene and natural atmosphere.
Home in Brewster
4.98 out of 5 average rating, 198 reviews

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

Guest favorite
A cozy living area features a brown sofa set, complemented by a rustic wooden coffee table at its center. A flat-screen TV is positioned on a white stand against the wall, while a rocking chair is visible in the corner. Soft natural lighting illuminates the space.
Guest suite in West Harwich
4.92 out of 5 average rating, 304 reviews

Cape Hideaway

Superhost
A lush garden is depicted with a variety of vibrant flowers and greenery, leading to a cozy screened porch adorned with string lights. People are seen enjoying the outdoor space, creating a welcoming atmosphere for gatherings amid the evening sky.
Home in Eastham
4.96 out of 5 average rating, 190 reviews

The Sea Captain's Carriage House

Guest favorite
An outdoor patio area features comfortable seating beneath a large umbrella. A grill is positioned nearby, while a spacious two-story house with light-colored shingles and numerous windows stands in the background, framed by greenery and an American flag.
Home in Harwich
4.87 out of 5 average rating, 152 reviews

Cozy and easy to beach & downtown

Other great vacation rentals in Chatham

Guest favorite
The renovated windmill exterior showcases unique architectural features with a pointed roof and prominent wooden blades. A bright blue door is framed by a brick pathway, leading to a garden of blooming daffodils, offering a cheerful first impression.
Cottage in Chatham
4.96 out of 5 average rating, 68 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

Top guest favorite
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.
Home in Chatham
5 out of 5 average rating, 79 reviews

Charming Chatham Home! Less than Mile To Beach !

Guest favorite
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
4.93 out of 5 average rating, 180 reviews

Cape Cod Classic Cottage Near Forest Beach

Guest favorite
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.
Home in Chatham
4.98 out of 5 average rating, 87 reviews

Beachfront Charmer! Newly Renovated.

Top guest favorite
An open concept living area features a comfortable white couch and armchair, with a wooden coffee table at the center. The kitchen, visible in the background, is well-equipped and includes a fridge, while a dining area with two stools is highlighted. Natural light brightens the space.
Vacation home in Chatham
5 out of 5 average rating, 55 reviews

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

Guest favorite
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.
Home in Chatham
5 out of 5 average rating, 19 reviews

Charming Chatham Cottage

Top guest favorite
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.
Home in Chatham
5 out of 5 average rating, 20 reviews

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

Guest favorite
A brightly lit living area features large windows adorned with soft shades. A striped sofa is complemented by a comfortable armchair and a light-colored coffee table. A flat-screen television is positioned against the wall, with framed artwork adding character to the space.
Apartment in Harwich
4.97 out of 5 average rating, 199 reviews

Cozy Apartment in Downtown Harwich Port

Quick stats about vacation rentals in Chatham

  • Total rentals

    600 properties

  • Nightly prices starting at

    G$12,547 GYD before taxes and fees

  • Total number of reviews

    18K reviews

  • Family-friendly rentals

    500 properties are a good fit for families

  • Pet-friendly rentals

    190 properties allow pets

  • Rentals with a pool

    40 properties have a pool

Frequently Asked Questions

  • Where should I stay in Chatham?

    Make yourself at home in Chatham by choosing from our most frequently booked neighborhoods. We have over 1,860 vacation rentals in East Harwich, and over 950 vacation rentals in Chatham.

  • Are there vacation rentals with a dedicated workspace in Chatham?

    Yes! Work meets play with ease at over 240 vacation rentals in Chatham featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chatham?

    Four-legged friends are welcome in Chatham. Choose from more than 190 vacation rentals for guests traveling with pets.

  • Do house rentals in Chatham have a bbq area?

    Absolutely! We offer over 230 house rentals with a bbq area in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Chatham have wifi?

    Absolutely! We offer over 10 condo rentals with wifi in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Are there Chatham house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 house rentals with pools in Chatham, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Chatham have a gym?

    Absolutely! We offer over 30 house rentals with a gym in Chatham. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly cottage rentals in Chatham?

    Chatham has more than 20 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Chatham?

    Experience the best of Chatham with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Chatham?

    Enhance your stay in our House Rentals with the most popular amenities: over 440 homes with wifi, over 30 homes with a gym, over 230 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore