Vacation rentals in Chatham, MA

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Chatham, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Chatham, MA

Best Chatham, MA vacation rentals with a balcony

A Contemporary Gem W/cape Character, Dog Friendly! - Chatham, MA
9.8 11 reviews

A Contemporary Gem W/cape Character, Dog Friendly!

apartment, Harwich
This Harwich seaside home boasts stunning ocean views and is located within two miles of Captain's Cove Golf Course, Cape Cod beaches, and three miles from Nickerson State Park.
This 1830-square-foot vacation rental features four bedrooms, two bathrooms, and accommodates eight guests, offering a fitness center, private terrace, and a fully equipped kitchen with a dishwasher.
Cape Cod Villa Pond Front Vacation Home, Retreat, Spa, Venue, Film Location - Chatham, MA
10 8 reviews

Cape Cod Villa Pond Front Vacation Home, Retreat, Spa, Venue, Film Location

house, Harwich
This Harwich lakefront villa is located within three miles of Nickerson State Park, Adventure Chatham, and two golf courses—Captains Golf Course and Captain's Cove Golf Course.
This five-bedroom, two-bathroom home sleeps eight guests and boasts a spa, game room, fully equipped kitchen, outdoor barbecue grills, and a terrace overlooking the lake, offering easy access to water activities.
Great Location Outdoor Space Dog Friendly - Chatham, MA
9.7 102 reviews

Great Location Outdoor Space Dog Friendly

apartment, Chatham
This vacation home is situated by the sea, within 2 miles of Hardings Beach, Cape Cod Beaches, and Veterans Field. It has excellent user, location, and cleanliness ratings.
The house has a floor area of 2250 square feet, 4 bedrooms, 3 bathrooms, and a guest capacity of 10. It features a spacious and well-equipped kitchen, a cozy fireplace, three bathrooms, a private garden, and gas grills. It offers stunning ocean views and is close to major tourist attractions in Chatham.
Ping-pong & Backyard: Spacious Chatham Retreat - Chatham, MA
No reviews

Ping-pong & Backyard: Spacious Chatham Retreat

house, Chatham
Vacation rental listing. You will stay in Chatham.
Facilities and services: free parking, a kitchen and air conditioning.

Search Family Vacation Rentals in Chatham, MA

Plan the perfect family beach trip to Chatham, MA with spacious rentals that offer plenty of room to spread out.

Cape Cod Classic Cottage Near Forest Beach - Chatham, MA
9.9 196 reviews

Cape Cod Classic Cottage Near Forest Beach

apartment, Chatham
This two-bedroom cottage is situated in a peaceful Chatham neighborhood, just a short walk from Forest Beach and a quick drive to downtown Chatham.
The cottage boasts a fully renovated interior with modern amenities, including a gas stove, quartz countertops, central AC, a large walk-in shower, a 50-inch Samsung Frame TV with streaming services, and a backyard with a deck, hammock, and EV charging.
Waterfront On Pond W/ Private Beach! - Chatham, MA
9.4 13 reviews

Waterfront On Pond W/ Private Beach!

house, Chatham
This waterfront house offers direct access to Schoolhouse Pond in Chatham, featuring a private beach and located a short drive from the town center.
This 2,500 sq ft home sleeps up to 9 guests and includes 4 bedrooms, 3 bathrooms, a fully equipped kitchen, WiFi, and a propane grill, with beds made upon arrival.
Central Ac Close To Beach Dog Friendly! - Chatham, MA
10 22 reviews

Central Ac Close To Beach Dog Friendly!

house, Chatham
This Maiden Chatham house is conveniently located a short drive from Ridgevale and Hardings Beaches, and 5 minutes from Downtown Chatham.
This dog-friendly rental accommodates up to 8 guests with 3 bedrooms, a lofted sleeping area, a game room featuring a ping pong table, and a backyard with a fire pit and gas grill.
Waterfront On Private Lake! - Chatham, MA
9.4 24 reviews

Waterfront On Private Lake!

house, Chatham
This waterfront house in central Chatham offers direct access to a private lake, perfect for kayaking and SUPing, and is a short 5 to 10-minute drive from Jackknife Beach and Harding's Beach. This family-friendly residence accommodates up to 9 guests across four bedrooms, featuring a newly renovated kitchen with Samsung stainless steel appliances, central and mini-split air conditioning, a downstairs game room, and multiple outdoor dining areas with lake views.

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Best Chatham, MA vacation rentals with parking

Quintessential Cape Cod Cottage - Chatham, MA
9.9 17 reviews

Quintessential Cape Cod Cottage

apartment, Chatham
This Chatham Cape Cod-style cottage is conveniently located near Harding's Beach and Ridgevale Beach, a short two-mile drive from downtown Chatham and the Chatham Farmers Market.
This two-bedroom, one-bathroom house sleeps four, features a fully equipped kitchen with a dishwasher, air conditioning, a pleasant outdoor shower and deck, and eco-friendly amenities including an RO water system; enjoy nearby restaurants and shops.
Beautiful Downtown Chatham 1 Bed, Near Oyster Pond - Chatham, MA
10 77 reviews

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

apartment, Chatham
This Chatham apartment rental is a one-minute walk from downtown Chatham's shops and restaurants, and a nine-minute walk from Oyster Pond Beach, placing you steps from Veterans Field (home of the Chatham Anglers) and other attractions.
The newly renovated one-bedroom, one-bathroom unit sleeps two guests and features a modern, open-concept kitchen with a dishwasher, microwave, and fridge, a private patio, smart TV, and convenient access to a nearby laundromat; on-site parking may be available.
Walk To Ridgevale Beach | Chatham Escape - Chatham, MA
9.8 103 reviews

Walk To Ridgevale Beach | Chatham Escape

apartment, Chatham
This Chatham home is located just a short walk from Ridgevale Beach, perfect for families looking for a relaxing seaside getaway. The property has received excellent ratings for location, cleanliness, and overall experience.
The 3-bedroom, 2-bathroom house can comfortably accommodate up to 8 guests. Enjoy modern amenities like central air, Wi-Fi, a fully equipped kitchen, washer/dryer, and a game room with foosball.
15 Minute Walk To Pleasant Street Beach! - Chatham, MA
9.6 86 reviews

15 Minute Walk To Pleasant Street Beach!

apartment, Chatham
This charming house is located in South Chatham, just a short walk from Cape Cod Beaches, Forest Beach, and the Chatham Chamber of Commerce. The house has excellent user, location, and cleanliness ratings, making it a perfect choice for your vacation.
This vacation home has 4 bedrooms, 2 bathrooms, and a floor area of 1820 square feet, comfortably accommodating up to 8 guests. The property features a garden, barbecue grills, a fully equipped kitchen, a washing machine, and modern amenities like a coffee/tea maker and a TV, providing everything you need for a relaxing and enjoyable stay.

Check Out Vacation Rentals with a Pool in Chatham, MA

Complement your time by the water with a dip in the pool at these Chatham, MA vacation rentals with on-site swimming facilities.

Luxury Home With Pool, Hot Tub & Water View - Chatham, MA
10 2 reviews

Luxury Home With Pool, Hot Tub & Water View

house, Chatham
This luxury house is located on a cove in Chatham, offering water views and is a 10-minute drive from downtown Chatham.
This five-bedroom, five-and-a-half-bathroom property accommodates up to 12 guests and features a heated swimming pool, hot tub, gas fire pit, and a chef's kitchen, with easy access to Jacknife Beach, Lighthouse Beach, Oyster Pond, and Pleasant Bay.
Wequassett Resort And Golf Club - Chatham, MA
9.3 367 reviews

Wequassett Resort And Golf Club

resort, Harwich
The Wequassett Resort And Golf Club is located in Harwich, a short drive from the town center and the Cape Cod National Golf Center. This resort has received excellent ratings for its location, user experience, and cleanliness.
The resort has spacious rooms with sitting areas and private decks or patios. Guests can enjoy a variety of amenities, including a swimming pool, hot tub, tennis court, fitness center, and restaurant, as well as a golf course and spa.
Luxury Home With Pool, Hot Tub & Water View - Chatham, MA
10 3 reviews

Luxury Home With Pool, Hot Tub & Water View

apartment, Chatham
This waterfront vacation home in North Chatham is a short walk from the Chatham Shark Center (11 minutes) and Chatham Marconi Maritime Center (15 minutes), offering proximity to marine attractions and local natural beauty.
This spacious 3,890 sq ft residence accommodates up to 12 guests with 5 bedrooms and 6 bathrooms, featuring a private garden, shared pool, hot tub, and essential amenities like Wi-Fi and air conditioning.
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok - Chatham, MA
No reviews

Walk 2beach, Pool, Hot Tub, Gameroom, Petsok

house, Chatham
This pet-friendly house in Chatham offers prime walkability to the beach, with Harding Beach just 1.2 miles away and the Cape Cod National Seashore 18 miles distant.
This 38,750 square foot estate accommodates 19 guests with 4 bedrooms, 4 bathrooms, a private pool, hot tub, game room, and on-site parking.

Browse Waterfront Vacation Rentals in Chatham, MA

Discover beautiful beach towns with these seaside vacation rentals in Chatham, MA, perfect for relaxing near the coast and exploring the shore.

Private Beach In Chatham - Sleeps 5 - Chatham, MA
9.8 141 reviews

Private Beach In Chatham - Sleeps 5

apartment, Chatham
Hot Tub, Fenced Yard & Dog Friendly - Chatham, MA
9.9 84 reviews

Hot Tub, Fenced Yard & Dog Friendly

apartment, Chatham
Great Location With Water Views! - Chatham, MA
9.0 6 reviews

Great Location With Water Views!

house, Harwich
143 M² House ∙ 3 Bedrooms ∙ 8 Guests - Chatham, MA
10 1 review

143 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Chatham

Compare Luxury Vacation Rentals in Chatham, MA

Discover the best of the coast with a luxury vacation rental in Chatham, MA, offering sophisticated rooms and prime locations.

Lovely Cape Cottage Home < 1 Mile To The Beach! - Chatham, MA
10 102 reviews

Lovely Cape Cottage Home < 1 Mile To The Beach!

apartment, Chatham

Discover Vacation Rentals with Saunas in Chatham, MA

Maximize your wellness with vacation rentals in Chatham, MA featuring on-site saunas and steam rooms.

Waterview/front Cottage - Chatham, MA
9.9 120 reviews

Waterview/front Cottage

apartment, Chatham
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