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Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

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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.

Home in Chatham

4.95 out of 5 average rating, 285 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.

Top guest favorite

The exterior of a spacious house is shown, featuring a large front porch with a gentle slope and decorative flowers. An attached garage is visible, and the well-manicured lawn surrounds the property. A private gravel driveway leads to the entrance, shaded by trees under a clear blue sky.

Guest suite in Chatham

4.99 out of 5 average rating, 125 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.

Top guest favorite

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.

Guest suite in Harwich

4.99 out of 5 average rating, 613 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.

Top guest favorite

A rustic, two-story cabin is surrounded by lush landscaping. A green door welcomes visitors, while a small stone pathway leads to a pair of outdoor chairs situated on a grassy lawn. The harmonious design includes natural stone walls and shaded trees.

Apartment in Chatham

4.96 out of 5 average rating, 272 reviews

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.

Cottage in Chatham

4.94 out of 5 average rating, 173 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.

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, 52 reviews

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!

Top guest favorite

The inviting living area features large windows with blue curtains, allowing natural light to brighten the space. A comfortable sectional sofa is situated around a small coffee table. A door leads to a private balcony, while a bar counter with stools is visible in the background.

Condo in Chatham

4.96 out of 5 average rating, 340 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**

An open-concept living area features a spacious blue sectional sofa and a flat-screen TV mounted on the wall. Natural light floods the room through large windows, offering views of the surrounding greenery. A decorative plant and a textured area rug add warmth to the space.

Condo in Chatham

4.86 out of 5 average rating, 109 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 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.

Home in Chatham

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

A cozy cottage exterior is displayed, featuring a light gray shingle facade and white trim around the windows. A screened-in porch is visible, accompanied by blue outdoor chairs. The surrounding area showcases a grassy yard with greenery and trees in the background.

Cottage in Chatham

4.9 out of 5 average rating, 151 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 !

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.

Home in Chatham

4.91 out of 5 average rating, 187 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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Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Chatham vacation rentals

Free parking on premises

Air conditioning

Chatham beach vacation rentals

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, 223 reviews

Serenity Views | Waterfront | KingBed | Kayaks SUP

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, 198 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

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, 234 reviews

WOW VIEW! Waterfront, Private 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, 133 reviews

Private Bay Beach and Sunset Views! Dog friendly.

A charming cottage is surrounded by lush greenery and soft landscaping. The exterior features a light wood shingle design with a welcoming porch and a shaded deck area. Outdoor seating is present, inviting relaxation under the clear blue sky.

Home in Hyannis Port

4.88 out of 5 average rating, 172 reviews

Cottage with private beach in Hyannis Port

The ocean front view features a rainbow arching over Cape Cod Bay, with a grassy area leading to the water. A swing set and a vehicle are visible in the foreground, while lush greenery borders the bay in the background.

Cottage in Plymouth

4.9 out of 5 average rating, 133 reviews

Ocean Front Cottage With A Million Dollar View

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, 286 reviews

Amazing WATERFRONT with Wood Fireplace! 4bdrm/2bth

Other great vacation rentals in Chatham

A private pool area is highlighted, featuring a rectangular pool surrounded by lounge chairs and umbrellas. Lush greenery and a white fence provide a serene backdrop, while the sun casts a warm glow over the inviting space.

Home in Chatham

4.95 out of 5 average rating, 22 reviews

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

A bright living area features a dark gray sectional sofa adorned with blue and white patterned cushions. A wooden dining table is positioned nearby, surrounded by four chairs. Large windows allow natural light to illuminate the space, enhancing the light-colored wood paneling.

Cottage in Chatham

4.94 out of 5 average rating, 53 reviews

Chit-Chat Cottage on White pond, near DT/beaches.

Top guest favorite

A charming exterior showcases a single-story unit with cedar shingle siding and light blue shutters. The entryway features a glass-paneled door, framed by bright windows. Two white adirondack chairs sit on a sandy area, surrounded by trees and a wooden fence.

Apartment in Chatham

5 out of 5 average rating, 9 reviews

Chatham Studio- .5 mile to beach

The exterior of the cottage features a wooden shingle facade, characterized by a unique pink-trimmed entrance and windows. Colorful flower pots line the entryway, complemented by vintage-style bikes. Tall trees provide a natural backdrop against the clear blue sky.

Cottage in Chatham

4.95 out of 5 average rating, 78 reviews

Chatham Rose Arbors Artist Cottage

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

4.95 out of 5 average rating, 66 reviews

Renovated Chatham Windmill! Walk to Beach/Town!

The exterior of a recently renovated house is shown, featuring blue siding and white trim. Two symmetrical green shrubs accompany the entrance, which has a red door adorned with a decorative wreath. Windows with red shutters provide a balanced look to the facade.

Home in Chatham

4.97 out of 5 average rating, 34 reviews

Chatham House Close to Beaches and Bike Path.

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, 73 reviews

Charming Chatham Home! Less than Mile To Beach !

A calm freshwater pond is surrounded by lush greenery and tall trees. A float is visible on the water, providing a serene spot for relaxation. Lilypads are scattered across the surface, reflecting the clear blue sky.

Home in Chatham

4.91 out of 5 average rating, 88 reviews

Spacious studio on lovely pond in Chatham

Quick stats about vacation rentals in Chatham

Total rentals
600 properties
Nightly prices starting at
ﺩ.ﺇ220 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

Do cabin rentals in Chatham have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Chatham. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Chatham have wireless internet?
Absolutely! We offer over 30 cottage rentals with wireless internet in Chatham. Enjoy a tailored experience with all the comforts you desire.
Are there house rentals with a dedicated workspace in Chatham?
Yes! Work meets play with ease at over 200 house rentals in Chatham featuring dedicated workspaces. Stay connected and productive in your home away from home.
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 cabin rentals in Chatham have self check-in?
Absolutely! We offer over 10 cabin rentals with self check-in in Chatham. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Chatham?
Four-legged friends are welcome in Chatham. Choose from more than 170 house rentals for guests traveling with pets.
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.
Where should I stay in Chatham?
Make yourself at home in Chatham by choosing from our most frequently booked neighborhoods. We have over 950 vacation rentals in Chatham, and over 1,860 vacation rentals in East Harwich.
What are the most popular amenities for Cabin Rentals in Chatham?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.

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