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Vacation rentals in Chatham

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Quick stats about vacation rentals in Chatham

  • Total vacation rentals

    Explore 570 vacation rentals in Chatham

  • Nightly prices starting at

    Chatham vacation rentals start at R 975 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 20,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    500 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 220 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    320 properties have a dedicated workspace

  • Wi-Fi availability

    560 of Chatham vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Beachfront, Gym, and BBQ grill across Chatham rentals

  • 4.9 Average rating

    Chatham stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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

Private Beach in Chatham - Sleeps 5

Welcome to 6 Starfish Lane! Rare for Chatham - flexible stays perfect for a long weekend and last minute getaways (2-4 night min, varies). This is a 2 Bedroom condo (King + Full + Twin) with views of the beach, ocean and marina. We have a private beachfront/oceanfront steps away and easy for the whole family! We are also within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous Lighthouse Beach and Monomoy Wildlife refuge. This is a great place to make memories!

FamilyLocationComfort

4.89 out of 5 average rating, 142 reviews
Guest favorite
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

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.

FamilyValueIndoor spaces

4.95 out of 5 average rating, 322 reviews
Top guest favorite
A charming cottage with a shingle exterior is framed by a vibrant yard. A white picket fence encloses flower beds, and a small patio features an umbrella for shade. A welcoming pathway leads to the front door, surrounded by greenery and a manicured lawn.
Cottage in Chatham

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

LocationValueAmenities

4.97 out of 5 average rating, 295 reviews
Top guest favorite
A charming single-story home is presented with light grey shingles and dark blue shutters. A paved pathway leads to the front door, framed by manicured green lawns and landscaped flower beds. Trees and shrubs add to the serene outdoor environment.
Cottage in Harwich Port

Newly renovated Cape Coddage! Location! Location!

Newly renovated! Harwichport home- 2 min walk to beach, sleeps 10. Located right by Bank St Beach In Harwichport! Walk 1-2 minutes to the beach or walk 1-2 minutes in the other direction to Main Street where you will find shops and restaurants. Ember, The Port, 3 Monkeys, Beer Garden, and Mad Minnow. This home is in the dream location. Pull in and you don't need to drive until you leave. Walkable to Wychmere beach club. This home is often shared by guests of events celebrated at Wychmere.

FamilyLocationLayout

4.95 out of 5 average rating, 432 reviews
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

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.

ValueFamilyGrill

4.96 out of 5 average rating, 311 reviews
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

Charming Chatham Home! Less than Mile To Beach !

Cozy,comfortable and completely renovated this cottage has everything you need for a relaxing stay. Central air, outdoor shower, deck with Weber grill, fire pit, fully stocked kitchen. All linens provided, including beach towels. Less than a mile to Forest Beach and bike path. Short drive to all popular beaches. 10 minutes to Chatham Center, 5 minutes to Harwichport Center. We are nearby should you need anything during your stay , however you have complete privacy. Keyless entry.

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 101 reviews
Top 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

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

FamilyLocationIndoor spaces

4.97 out of 5 average rating, 120 reviews
Top guest favorite
A bright living area features large windows overlooking a scenic marshland and ocean view. A cozy cream-colored couch and an armchair are positioned near a glass coffee table, inviting relaxation. Natural light fills the space, enhancing the tranquil ambiance.
Home in Chatham

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

FamilyValueComfort

4.97 out of 5 average rating, 178 reviews
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

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.

FamilyValueHiking

4.93 out of 5 average rating, 197 reviews
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

Private Pied-a-Terre, in-village hidden Oasis.

Great in-town location. Bright, Clean, Safe, Private and Spacious. Hidden away Above the 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. Well equipped 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**

LocationFamilyWifi

4.97 out of 5 average rating, 409 reviews
Top guest favorite
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

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

FamilyLocationLayout

4.97 out of 5 average rating, 103 reviews
Guest favorite
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

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).

LocationValueCheck-in

4.91 out of 5 average rating, 209 reviews

Popular amenities for Chatham vacation rentals

BeachfrontGymBBQ grillLaptop-friendly workspaceWifi

Stay near Chatham's top sights

Chatham Lighthouse

158 locals recommend

Lighthouse Beach

115 locals recommend

Monomoy National Wildlife Refuge

54 locals recommend

Harding Beach

52 locals recommend

Chatham Candy Manor

46 locals recommend

Red River Beach

45 locals recommend

Chatham beach vacation rentals

Guest favorite
Cottage in Harwich Port

2BR Directly on Pleasant Beach – 30 Steps to Ocean

ValueLocationBathroom

4.82 out of 5 average rating, 129 reviews
Top guest favorite
A charming two-story home is framed by vibrant greenery and colorful shrubs, with a paved pathway leading to the entrance. Solar panels adorn the roof, reflecting a commitment to sustainability. Lush grass and well-maintained landscaping create an inviting atmosphere.
Home in Falmouth

Private Pond-side Cape Cod Home

ValueLocationBackyard

5.0 out of 5 average rating, 172 reviews
Superhost
An outdoor seating area is presented with a fire table at its center, illuminated by flames. Comfortable chairs surround the fire, with a red umbrella providing shade above. The ocean and sunset create a serene backdrop, showcasing vibrant colors across the sky.
Cottage in Sandwich

Bold Oceanfront Cottage w/Pvt Beach ~ Lil Sea Sass

ValueLocationWalkability

4.85 out of 5 average rating, 470 reviews
Top guest favorite
Cottage in West Yarmouth

Cozy Coastal Cottage With Sprawling Sea Views

ValueFamilyCleanliness

4.97 out of 5 average rating, 277 reviews
Guest favorite
The cottage, surrounded by mature landscaping, is located near a private beach. A sandy expanse is visible in the background, highlighting the close proximity to the shore. Nearby structures exhibit a rustic charm, contributing to the serene beach environment.
Cottage in Sandwich

Hideout at Water's Edge, 131 North Shore Blvd, #4

LocationFamilyLayout

4.92 out of 5 average rating, 319 reviews
Top guest favorite
The exterior of a spacious coastal property is shown, featuring a wraparound porch and light grey shingle siding. A clear blue sky complements the beach setting, with soft sand leading to the ocean in the background. Lush greenery borders the property, providing a sense of seclusion.
Home in Sandwich

Salt Eire | Oceanfront Beach Home

FamilyLocationComfort

4.99 out of 5 average rating, 158 reviews
Guest favorite
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

Cottage with private beach in Hyannis Port

ValueFamilyComfort

4.91 out of 5 average rating, 232 reviews
Top guest favorite
Home in Yarmouth Port

Sauna · Fireplace · Waterfront · 2 Kings · DogsYes

FamilyValueCheck-in

4.99 out of 5 average rating, 133 reviews

Chatham house rentals

Top guest favorite
A spacious, modern kitchen area features a large island with a dark base and white countertops, accented by pendant lights above. To the side, an open concept living space includes a comfortable seating arrangement and dining area, with natural light streaming in through large windows.
Home in Harwich

Spacious cottage beach Wychmere < 4 min Central AC

LocationFamilyCleanliness

4.99 out of 5 average rating, 137 reviews
Top guest favorite
The exterior of the coastal retreat features a welcoming entrance with a brick pathway leading to a charming blue door. Lush green grass surrounds the home, adorned with vibrant hydrangea bushes in shades of blue and lilac on either side.
Home in Chatham

Lovely Cape Cottage Home < 1 mile to the beach!

FamilyLocationWalkability

5.0 out of 5 average rating, 103 reviews
Top guest favorite
A modern kitchen features stainless steel appliances and a tiled backsplash, with a clear view of the adjoining dining area. Soft overhead lighting illuminates the space, complemented by hardwood flooring. A large window allows natural light to enhance the inviting atmosphere.
Home in Chatham

Spacious Pet Friendly Cape, Large Yard

FamilyLocationHiking

4.95 out of 5 average rating, 106 reviews
Guest favorite
Home in Chatham

Walk to Ridgevale Beach | Chatham Escape

LocationValueLayout

4.91 out of 5 average rating, 103 reviews
Guest favorite
A bright bedroom showcases a spacious bed with white linens and decorative pillows. A wooden dresser and bedside tables are positioned nearby. Nautical-themed decor, including a wall sign and a decorative ship's wheel, enhances the coastal ambiance. Natural light enters through a window overlooking the peaceful surroundings.
Home in Chatham

Walk to Ridgevale Beach

LocationFamilyBeach

4.94 out of 5 average rating, 138 reviews
Guest favorite
The cottage exterior features a light brown facade with white trim, complemented by blooming hydrangeas in shades of blue and purple. A front porch with white railings invites relaxation, while an American flag is displayed. A spacious gravel driveway leads up to the entrance.
Home in Chatham

Cute cottage - walking distance to Ridgevale Beach

FamilyLocationWifi

4.88 out of 5 average rating, 151 reviews
Top guest favorite
A sandy beach area is shown, populated with visitors enjoying the sun and water activities. Small boats are visible in the distance, while people are seen wearing casual summer attire. Beach chairs and umbrellas are scattered throughout the shoreline.
Home in Chatham

The Chatham Bars White Foam House Steps From Beach

FamilyLocationComfort

5.0 out of 5 average rating, 29 reviews
Top guest favorite
Home in Chatham

Meadow + Main

ValueLocationAccuracy

5.0 out of 5 average rating, 28 reviews

Beach house rentals in Chatham

Guest favorite
A sandy beach area is captured, featuring soft dunes and gentle ridges formed by the wind. A building with a distinctive cupola is visible in the distance, surrounded by wooden walkways. Clear blue skies complement the serene coastal setting.
Home in Centerville

#25 Seasonal Cottage is 200 feet from the Beach

ValueFamilyComfort

4.9 out of 5 average rating, 135 reviews
Guest favorite
The exterior of a charming Cape house is visible, featuring a light-colored shingle facade and a distinct triangular roof. A welcoming porch adorned with white latticework provides seating. The setting is enhanced by a clear blue sky, with nearby trees offering a touch of greenery.
Home in West Yarmouth

Beach House, Harbor View and Family Friendly.

ValueFamilyCheck-in

4.89 out of 5 average rating, 539 reviews
Guest favorite
A serene waterfront view captures a colorful sunset over the bay. Two white adirondack chairs are positioned on the grassy area, facing the water. Gentle waves lap against a stone structure, while a small boat is seen in the distance.
Home in Buzzards Bay

Beautiful ocean front home with amazing view

FamilyLocationBackyard

4.89 out of 5 average rating, 155 reviews
Top guest favorite
An open floor plan living area features a light-colored sofa adorned with teal accent pillows, complemented by a plush gray rug. Large windows provide a view of the ocean, while a dining area is visible in the background, surrounded by wooden beams and natural light.
Home in Buzzards Bay

Relax by the Sea, Cozy 2 bedroom home

ValueLocationQuiet

4.92 out of 5 average rating, 106 reviews
Top 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.
Home in Sandwich

WOW LAKE VIEW! Waterfront with Beach, King Bed

FamilyValueBathroom

4.96 out of 5 average rating, 284 reviews
Guest favorite
Home in Brewster

3BR Pond Views | Private Beach & Kayaks

LocationFamilyCleanliness

5.0 out of 5 average rating, 7 reviews
Top guest favorite
An outdoor dining area features a large table surrounded by chairs under a shaded umbrella. A grill is visible in the background, while a view of the ocean is framed by greenery. The area is bathed in natural light with a clear blue sky overhead.
Home in North Eastham

Bay Dreams! Panoramic Bay Views!

ValueFamilyKitchen

5.0 out of 5 average rating, 17 reviews
Top guest favorite
Home in Sandwich

The Gilded Anchor

LocationFamilyCheck-in

4.97 out of 5 average rating, 31 reviews

When is the best time to visit Chatham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 4,792 ZARR 4,954 ZARR 5,035 ZARR 5,458 ZARR 5,929 ZARR 7,602 ZARR 8,934 ZARR 8,934 ZARR 6,059 ZARR 5,474 ZARR 5,718 ZARR 5,604 ZAR
Avg. temp0°C0°C3°C7°C12°C17°C21°C21°C18°C13°C8°C3°C

Frequently Asked Questions

  • What are the best places to stay in Chatham?

    Chatham has a range of stays near beaches, the historic village area, and Main Street. Many visitors seek accommodations with scenic views or easy access to local shops and trails.

  • What are the best things to do in Chatham with kids?

    Families often explore sandy beaches, interactive museums, and nature trails. Chatham also has casual dining options and ice cream shops that welcome kids.

  • What are some of the best things to do in Chatham?

    Explore sandy beaches, visit the iconic lighthouse, and stroll the shops and galleries along Main Street. Nature reserves and boat tours show coastal habitats, offering a variety of outdoor experiences.

  • How is the weather in Chatham?

    Chatham has chilly, wetter winters near 25–44°F (-4–7°C), while summers are mild and bring temperatures between 63–76°F (17–24°C). Layers and a waterproof jacket are useful year-round.

  • When is the best time to visit Chatham?

    Late spring through early autumn is often recommended for milder temperatures between 48–76°F (9–24°C) and generally fewer rainy days. Summer draws visitors for beaches and seasonal festivities.

  • What are the best places to visit in Chatham?

    Chatham Lighthouse, Main Street's shops and galleries, and sandy beaches are frequently suggested. Local museums and conservation areas invite exploration of maritime history and nature.

  • What are some hiking trails in Chatham?

    Chatham has nature trails winding through salt marshes, woodlands, and conservation lands. Community parks and protected areas are often suggested for gentle hikes and birdwatching.

  • What are some family activities we can do in Chatham?

    Visit sandy beaches, play in community parks, tour maritime museums, and spot seals near the lighthouse. Seasonal events and outdoor picnics on trails are often enjoyed by families.

  • What are some of the best day trip ideas from Chatham?

    Explore nearby Cape Cod towns, local nature reserves, or take a ferry to see coastal islands. Art galleries, historic sites, and outdoor adventures are frequently suggested for day trips around the area.

  • Are there any pet friendly accommodations available in Chatham?

    Many accommodations in Chatham welcome pets, especially around Main Street, the village area, and beach neighborhoods. Parks and walking trails make it easy to get outside with your dog.

  • What are some local tips for visiting Chatham?

    Locals often suggest booking popular restaurants and activities in advance during summer. Early morning beach walks and exploring markets around Main Street are favorites for a quieter experience.

  • What is Chatham known for?

    Chatham has sandy beaches, a scenic lighthouse, and a lively pedestrian-friendly Main Street. It is often recognized for its maritime history, local seafood, and coastal charm.

  • What are the best hidden gems to explore in Chatham?

    Walk through serene conservation areas, discover tucked-away art galleries, or find quiet coves for beachcombing. Small markets and lesser-known nature trails around Chatham reward curious explorers.

  • What are the best foods to try in Chatham?

    Locally caught seafood is frequently suggested, including clam chowder, lobster rolls, and oysters. Bakeries and ice cream shops around Main Street feature seasonal treats and classic desserts.

  • What should I bring for a trip to Chatham?

    Pack layers, a light waterproof jacket, and comfortable walking shoes for strolling beaches or exploring town. Sunscreen, hats, and reusable water bottles are handy for outdoor activities.

  • What is the nightlife in Chatham like?

    Chatham has casual nightlife centered around pubs, restaurants, and occasional live music spots. Evening gatherings often highlight seasonal outdoor concerts and relaxed dining.

  • What are the most popular events or festivals in Chatham?

    Chatham has summer art fairs, Fourth of July parades, and holiday strolls in winter. Local concerts and community celebrations are often recommended, especially during peak visitor seasons.

  • Are there family friendly vacation rentals in Chatham?

    Chatham has a range of family friendly vacation rentals, including cottages, larger homes, and condos near beaches and downtown. Many stays feature amenities like backyards and proximity to parks.

Destinations to explore