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

Luxury Waterfront With Game Room! - Chatham, MA
8.8 3 reviews

Luxury Waterfront With Game Room!

apartment, Chatham
This North Chatham vacation rental boasts a waterfront location on Crows Pond, a mile from Jacknife Beach, and convenient access to Chatham's Main Street, offering proximity to attractions like the Chatham Marconi Maritime Center.
This 3,270-square-foot home features five bedrooms, four bathrooms, and accommodates up to twelve guests, complete with a game room, updated kitchen, private patio, outdoor shower, and ample parking.
Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-newly Renovated Private Retreat Ac - Chatham, MA
10 1 review

Cape Escape Chatham 5 Star Beach Chic 5 Min Walk To Beach-newly Renovated Private Retreat Ac

house, Chatham
This newly renovated house in Chatham offers unbeatable proximity to the beach, just a 5-minute walk away, and is a 17-minute walk from Forest Beach, with Nauset Lighthouse 15 miles distant.
This spacious 1700 square foot vacation home accommodates up to 18 guests with 3 bedrooms and 2 bathrooms, featuring a shared kitchen, barbecue, complimentary bikes, outdoor play equipment, and private beach access.
Sweeping Views, 150 Yards To Private Beach! - Chatham, MA
8.8 5 reviews

Sweeping Views, 150 Yards To Private Beach!

apartment, Chatham
This five-bedroom Chatham vacation home, located in North Chatham, is approximately 150 yards from a private beach and 1.3 miles from the Town Landing Beach.
This 2,500-square-foot rental boasts four bathrooms, a private terrace, and parking for four cars, comfortably accommodating up to twelve guests with amenities including a gas fireplace, propane grill, and smart TV.
Walk To Pleasant St Beach! - Chatham, MA
10 1 review

Walk To Pleasant St Beach!

cottage, Chatham
This South Chatham cottage is a short walk from South Chatham village and a beautiful beach, near the Caleb Nickerson House and Chatham Lighthouse Beach.
This three-bedroom, two-bathroom house sleeps six, features central air conditioning, a terrace, parking, Wi-Fi, and a large yard perfect for outdoor activities, plus a sunroom; nearby attractions include the Cape Cod Lavender Farm and Cape Cod Baseball & Bumper Boats.

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.

Modern Kitchen And Outdoor Patio Bliss - Charming Getaway - Chatham, MA
9.4 3 reviews

Modern Kitchen And Outdoor Patio Bliss - Charming Getaway

house, Chatham
This Chatham vacation home offers a classic Cape Cod experience, situated 0.6 miles from Schoolhouse Pond, 3.2 miles from Hardings Beach, and 1.2 miles from the Cape Cod Rail Trail.
This family-friendly ranch-style house accommodates up to four guests with two bedrooms and two bathrooms, featuring air conditioning, internet, a full kitchen with a dishwasher, and includes complimentary Xplorie activities like Island Cruises and Whale Watch.
80 M² Cottage ∙ 1 Bedroom ∙ 4 Guests - Chatham, MA
9.6 21 reviews

80 M² Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage, Chatham
This beachfront Chatham cottage sits on Goose Pond, a short drive (2.6 miles) from downtown Chatham's shops and restaurants, including the Orpheum Theater and Chatham Bars Inn, and 2 miles from Ridgevale Beach on Nantucket Sound.
This 860-square-foot getaway, boasting one bedroom and one bathroom, comfortably sleeps four guests and includes two kayaks, a spa, fitness center, a newly updated kitchen and bathroom, an outdoor shower, and a welcome bag with Xplorie access to local attractions.
Chatham Break! 3 Br, A/c, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard - Chatham, MA
10 108 reviews

Chatham Break! 3 Br, A/c, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

apartment, Chatham
This Chatham vacation home, near Oyster Pond, offers a quiet location on a dead-end road, a 3-minute walk from shops and restaurants, 1.3 miles from downtown Chatham, and 1.7 miles from Hardings Beach.
The 1,000-square-foot house features three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, laundry facilities, a private yard with a gas grill, and beach gear.
65 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chatham, MA
10 1 review

65 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Chatham
This pet-friendly Chatham cottage is located in a private neighborhood, a short 0.3-mile walk from Ridgevale Beach and a few miles from Chatham's town center.
The 690-square-foot home features two bedrooms, one bathroom, sleeps four, includes a kitchen with a fridge and microwave, offers an outdoor space with a fire pit, and comes with a $750 Xplorie package for local attractions.

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Best Chatham, MA vacation rentals with parking

Chatham Getaway - Chatham, MA
9.9 161 reviews

Chatham Getaway

house, Chatham
This Chatham Cape Cod guest house is ideally located one block from downtown Chatham, providing easy access to shops, restaurants, the Chatham movie theater, Oyster Pond Beach, Chatham Links golf course, and the Chatham Bars Inn.
The 1-bedroom, 1-bathroom cottage offers self check-in, sleeps four guests, and features a spacious layout with upstairs bedroom and loft, downstairs bathroom, and access to a private garden and parking.
Beautiful Home W Artistic Flair - Chatham, MA
10 1 review

Beautiful Home W Artistic Flair

house, Chatham
This Chatham vacation home, near Ridgevale and Cockle Cove Beaches (1.5 and 1.7 miles away), offers easy access to Cape Cod National Seashore (22 miles) and Truro Historical Museum (29 miles).
This 1,540-square-foot house features three bedrooms, three bathrooms, and accommodates up to 13 guests, complete with a fully equipped kitchen, Wi-Fi, air conditioning, a private garden, parking, and a washing machine.
Chatham, Ma 258 Orleans Rd - 4br Loft-beauty! - Chatham, MA
9.7 59 reviews

Chatham, Ma 258 Orleans Rd - 4br Loft-beauty!

apartment, Chatham
This Chatham apartment rental is located one mile from Chatham's town center, Chatham Harbor, and the Chatham Bars Inn, offering easy access to shops, restaurants, and the waterfront.
The four-bedroom, two-bathroom house, featuring a detached loft, comfortably sleeps eight guests and includes a fully equipped kitchen with a dishwasher, air conditioning, a fenced-in yard, and ample parking.
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.

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.

Pool, Half Mile To Beach! - Chatham, MA
10 3 reviews

Pool, Half Mile To Beach!

house, Harwich
This Harwich rental house is located on a hill, offering 2,640 feet of access to Jackknife Beach and 0.4 miles to Wequassett Resort, with downtown Chatham shops and restaurants 3 miles away.
This family-friendly, pet-friendly home accommodates 10 guests in 5 bedrooms and 3.5 bathrooms, featuring central air conditioning, a private outdoor pool, an air hockey table, a ping pong table, and WiFi.
Wequassett Resort And Golf Club - Chatham, MA
9.3 366 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.
7-br Retreat Pool, Hot Tub, Sauna, Barn - Chatham, MA
10 1 review

7-br Retreat Pool, Hot Tub, Sauna, Barn

house, Chatham
This Chatham vacation home, near Ridgevale Beach (1.1 miles) and Cockle Cove Beach (1.5 miles), offers easy access to Cape Cod's beautiful beaches and attractions like the Nauset Lighthouse (15 miles) and Cape Cod National Seashore (23 miles).
This 4,000-square-foot property boasts seven bedrooms, four bathrooms, and accommodates up to 20 guests, featuring a private pool, spa, and fully equipped kitchen with modern appliances; additional amenities include free Wi-Fi, cable TV, a fireplace, and a washing machine.
Chatham Family Retreat W/ Heated Pool - Chatham, MA
10 2 reviews

Chatham Family Retreat W/ Heated Pool

apartment, Chatham
This Chatham vacation home is located a 3-minute drive from Cape Cod Beaches and an 11-minute walk from the Chatham Drama Guild, with proximity to Chatham Seaside Links and Captain's Cove Golf Course.
This spacious 5-bedroom, 5-bathroom apartment offers 2740 square feet of living space for up to 12 guests, featuring a private swimming pool, a terrace with a barbecue, complimentary Wi-Fi, and a fully equipped kitchen.

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.

Walk To Ryder Cove Wet Bar & Hot Tub - Chatham, MA
No reviews

Walk To Ryder Cove Wet Bar & Hot Tub

house, Chatham
Elegant Chatham Home Steps To Association - Charming Coastal Retreat - Chatham, MA
9.6 17 reviews

Elegant Chatham Home Steps To Association - Charming Coastal Retreat

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

143 M² House ∙ 3 Bedrooms ∙ 8 Guests

house, Chatham
Riviera Sunset - Chatham, MA
9.2 7 reviews

Riviera Sunset

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.

Close To Beach, Dog Friendly, Chatham Cottage - Chatham, MA
9.9 36 reviews

Close To Beach, Dog Friendly, Chatham Cottage

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.

Chatham Family Vacation - Chatham, MA
9.9 49 reviews

Chatham Family Vacation

apartment, Chatham
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