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Chatham, MA accommodations
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1112 Lodgings in Chatham, MA

Our Favorite Lodgings with a Pool in Chatham, MA

Choosing a lodging in Chatham, MA with a pool means you’ll always have a swimming option to complement a day by the water.

Chatham Bars Inn - Chatham, MA
9.2 1098 reviews
Chatham, MA
08/15 – 08/22
$11670/nighttotal: $81690 (7 )

Chatham Bars Inn

5 10
resort , Chatham
Chatham Bars Inn sits directly on the Atlantic Ocean in the charming town of Chatham, Massachusetts, offering stunning ocean views and easy access to the beach. The resort has consistently received excellent ratings for its location, user experience, and cleanliness.
The inn features a variety of accommodations, from cozy rooms to spacious suites. Guests can enjoy a range of amenities, including a heated pool, a private beach, a spa, a fitness center, and multiple dining options.
Enjoy Harwich, Pool, Large Hot Tub & Ac! - Chatham, MA
Chatham, MA
09/22 – 09/29
$1196/nighttotal: $8372 (7 )

Enjoy Harwich, Pool, Large Hot Tub & Ac!

1 4
house , Harwich
This Harwich house is located 15 miles from the Cape Cod National Seashore, 12 miles from Nauset Lighthouse, and 13 miles from Wellfleet Bay Wildlife Sanctuary.
This 2060 sq ft residence accommodates up to 31 guests with 1 bedroom and 3 bathrooms, offering a private balcony, a hot tub, air conditioning, a fully equipped kitchen, and complimentary Wi-Fi and parking.
Wequassett Resort And Golf Club - Chatham, MA
9.3 275 reviews
Chatham, MA
08/15 – 08/22
$6036/nighttotal: $42252 (7 )

Wequassett Resort And Golf Club

3 10
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.
Heated Pool Ac 1 2 Mile To Beach - Chatham, MA
Chatham, MA
08/15 – 08/22
$3187/nighttotal: $22309 (7 )

Heated Pool Ac 1 2 Mile To Beach

8 10
house , Harwich
This Harwich vacation home, a short walk from Forest Beach and Red River Beach, is conveniently located 14 miles from Cape Cod Gateway Airport and within a 14-mile radius of the Nauset Lighthouse.
This spacious 8-bedroom house boasts 2990 square feet of living space, accommodating up to 39 guests, and features a heated outdoor pool, a full kitchen with dishwasher, free Wi-Fi, and a private entrance.

Best family friendly Chatham, MA lodging

Among the 1112 accommodations in Chatham, MA, here are the 4 best for families

Beach Chic Chatham 5 Star 5 Min Walk To Beach-newly Renovated Private Retreat Ac - Chatham, MA
10 128 reviews
Chatham, MA
10/05 – 10/17
$558/nighttotal: $6696 (12 )

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

4 3
apartment , Chatham
This family-friendly vacation home is located in South Chatham, just a 15-minute walk from the Chatham Chamber of Commerce and Cape Cod Beaches. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
This spacious house offers 1,500 square feet of living space and can comfortably accommodate up to 10 guests. Enjoy a range of amenities, including a private swimming pool, a spa tub, a game room, and a garden with barbecue grills, perfect for relaxing and entertaining.
265 M² House ∙ 4 Bedrooms ∙ 11 Guests - Chatham, MA
9.8 10 reviews
Chatham, MA
06/17 – 06/24
$781/nighttotal: $5467 (7 )

265 M² House ∙ 4 Bedrooms ∙ 11 Guests

4 2
house , Harwich
Norma's Cape Escape, a spacious three-story house in Harwich, Massachusetts, is a short drive from Harwich Port beaches, Wequassett Resort (1.3 miles), and offers easy access to Dunkin', Starbucks, and Stop & Shop (1.7 miles).
This 2850-square-foot home sleeps 11, features 4 bedrooms, 3 bathrooms, a private spa, fitness center, and includes a $750 Xplorie package offering access to local attractions like Island Cruises and the Whydah Pirate Museum.
Dog Friendly Fenced In Yard! 3/2  1.1 Mi To  Wifi - Perfect Fall Rental! - Chatham, MA
10 71 reviews
Chatham, MA
09/22 – 09/29
$623/nighttotal: $4361 (7 )

Dog Friendly Fenced In Yard! 3/2 1.1 Mi To Wifi - Perfect Fall Rental!

4 4
apartment , Chatham
This spacious 3-bedroom vacation home is located in the heart of South Chatham, within walking distance of Chatham Chamber of Commerce and Cape Cod Beaches. It has received excellent ratings for its location, cleanliness, and user experience.
The house has a floor area of 1190 square feet and can accommodate up to 8 guests. It features a fully equipped kitchen, comfortable living space, free WiFi, and a sofa bed. Guests can also enjoy amenities such as a swimming pool, terrace, garden, spa, and parking.
Centrally Located Home With Patio, A/c Included, Walking Distance From Town. - Chatham, MA
10 30 reviews
Chatham, MA
06/20 – 06/27
$752/nighttotal: $5264 (7 )

Centrally Located Home With Patio, A/c Included, Walking Distance From Town.

3 3
apartment , Chatham
This Chatham vacation rental is centrally located, within walking distance of White's Pond beach and the Chatham bike path, offering easy access to public tennis and basketball courts.
This 2,000-square-foot home features three bedrooms, two bathrooms, and can comfortably accommodate eight guests, boasting a spacious open-plan living area, a finished basement with family room, and a newly renovated outdoor space complete with a patio, fire pit, and outdoor shower.

Frequently Asked Questions about accommodations in Chatham, MA

  • What are the must-see sites in or near Chatham, MA?

    Chatham is full of charm! You've got to see the Chatham Lighthouse, a classic New England landmark. The Chatham Bars Inn is also a popular spot, known for its beautiful grounds. And don't forget to take a stroll along the Chatham Fish Pier, where you can watch the local fishermen bring in their catch.
  • What are the best accommodations in Chatham, MA?

    Among the accommodations in Chatham, MA, #3 (1 King Bed With Private Bath In Room), Chatham Wayside Inn and Chatham Tides are the most popular ones.

  • How can travelers reach Chatham, MA?

    The easiest way to get to Chatham is by car. It's a scenic drive from Boston, about a 2-hour drive down the coast. You can also fly into Boston Logan International Airport (BOS) and rent a car. If you're coming from Cape Cod, you can take the scenic Route 6A, which passes through a lot of charming towns.
  • What are the best accommodations with a pool in Chatham, MA?

    Chatham Wayside Inn, The Chatham Motel and Chatham Seafarer Inn are the best accommodations with a pool in Chatham, MA.

  • What outdoor activities can visitors enjoy in and around Chatham, MA?

    Chatham is a haven for outdoor enthusiasts. You can spend the day at Chatham Beach, known for its beautiful white sand and clear waters. For a more adventurous experience, try kayaking or paddleboarding in the Chatham Harbor. And don't forget to visit the Chatham Light Beach, a popular spot for surfing and windsurfing.
  • What are the best accommodations with a jacuzzi in Chatham, MA?

  • When is the ideal time to plan a trip to Chatham, MA?

    The best time to visit Chatham is during the shoulder seasons, from April to May and September to October. The weather is still pleasant, but the crowds are smaller and prices are lower. You can enjoy the beautiful fall foliage in the fall and the vibrant spring blooms in the spring.
  • What are the best accommodations for families and kids in Chatham, MA?

    The best accommodations for families and kids in Chatham, MA are Chatham Wayside Inn, The Chatham Motel and Waterfront Chatham Village - Short Walk To Town & Lighthouse Beach.

  • What are the best walking or cycling routes in Chatham, MA?

    For a leisurely stroll, try the Chatham Rail Trail, a paved path that runs along the former Cape Cod Railroad. It's a great way to see the beautiful scenery of Chatham and the surrounding area. For a more challenging ride, try the Chatham to Orleans bike path, which stretches along the coast for about 10 miles.
  • What are the best pet friendly accommodations in Chatham, MA?

  • What nearby towns or cities can be explored from Chatham, MA?

    You can easily explore the charming towns of Harwich Port, Orleans, and Dennis from Chatham. Each town has its own unique character and attractions. For a bigger city experience, you can head to Hyannis, which is about 30 minutes away and has a bustling downtown area and a ferry terminal to Nantucket and Martha's Vineyard.
  • What are the best accommodations with parking in Chatham, MA?

    #3 (1 King Bed With Private Bath In Room), Chatham Wayside Inn and Chatham Tides are the best accommodations with parking in Chatham, MA.

  • What amenities can travelers expect from accommodations in Chatham, MA?

    Chatham offers a range of accommodations, from cozy bed and breakfasts to luxurious hotels. Many accommodations offer amenities like swimming pools, hot tubs, and fitness centers. Some also have restaurants and bars on-site. You can find options that fit your budget and preferences.

Destinations nearby

Best Chatham, MA accommodation with a balcony

Sophisticated Chatham Oasis With Pool & Spa Rpam062 - Chatham, MA
10 8 reviews
Chatham, MA
10/05 – 10/17
$3060/nighttotal: $36720 (12 )

Sophisticated Chatham Oasis With Pool & Spa Rpam062

5 3
apartment , Chatham
This luxurious Chatham vacation home is situated 0.3 miles from Main Street, providing easy access to shops, restaurants, and attractions like the Chatham Marconi Maritime Center and Cape Cod National Seashore.
This 7,000-square-foot, three-level residence boasts five bedrooms, nine bathrooms, and accommodates up to twelve guests, featuring a private heated pool, spa, game room with ping-pong and billiards, and a gourmet kitchen with a large island.
Classic Home With Deck, Patio & Yard - Walk To Cockle Cove & Forest Beaches - Chatham, MA
9.8 53 reviews
Chatham, MA
09/22 – 09/29
$562/nighttotal: $3934 (7 )

Classic Home With Deck, Patio & Yard - Walk To Cockle Cove & Forest Beaches

3 4
apartment , Chatham
This South Chatham residence is located a short walk to Forest Beach and one block from Main Street, offering 1490 square feet of living space.
This 3-bedroom, 2-bathroom condo accommodates up to 6 guests and features free WiFi, a full kitchen with a dishwasher, a gas grill, and a fenced yard.
Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc. - Chatham, MA
8.0 1 review
Chatham, MA
06/20 – 06/27
$1103/nighttotal: $7721 (7 )

Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc.

3 3
apartment , Chatham
This 3-bedroom, 3-bathroom condo is located in Chatham's downtown village, a short walk to shops and restaurants, and approximately 0.3 miles from Lighthouse Beach.
This residence accommodates up to 6 guests and features central air conditioning, complimentary Wi-Fi, and 5 televisions, with proximity to Cape Cod Beaches and Nauset Beach.
Guest House Ocean Whisper - Chatham, MA
9.7 4 reviews
Chatham, MA
06/20 – 06/27
$1035/nighttotal: $7245 (7 )

Guest House Ocean Whisper

4 3
house , Harwich
Guest House Ocean Whisper is a beachfront property in Harwich, just 12 miles from Nauset Lighthouse and 19 miles from Wellfleet Bay Wildlife Sanctuary. The property boasts excellent user, location, and cleanliness ratings, ensuring a pleasant stay.
The house offers 3 bedrooms and 1 bathroom, spanning 1210 square feet and accommodating up to 13 guests. Enjoy features like a private balcony, a fully equipped kitchen, air conditioning, a garden, parking, and a shared kitchen and luggage storage area for added convenience.

Best Chatham, MA accommodation with a kitchen

Sleep Under The Stars, Walk To Beach Chatham - Chatham, MA
10 45 reviews
Chatham, MA
10/05 – 10/17
$429/nighttotal: $5148 (12 )

Sleep Under The Stars, Walk To Beach Chatham

1 3
apartment , Chatham
This Cape Cod farmhouse rental near Harding's Beach and Barn Hill Landing in Chatham, Massachusetts, offers easy walking access to restaurants, shops, and kayaking/paddleboarding launch points, with downtown Chatham three miles away.
The four-bedroom house, sleeping six, features a kitchen with a fridge, microwave, and dishwasher; a terrace/balcony; a private yard with a firepit and gas grill; a screened sleeping porch; and ample parking, including space for boat trailers.
Beautiful Chatham Ma - Chatham, MA
9.9 15 reviews
Chatham, MA
06/18 – 06/27
$910/nighttotal: $8190 (9 )

Beautiful Chatham Ma

1 2
apartment , Chatham
This Ryder's Cove house in Chatham, MA, is conveniently located 0.5 miles from Jack Knife Beach, 1 mile from the Wequassett Resort, and within a short drive of other Chatham attractions.
The 3-bedroom main house plus a 1-bedroom in-law apartment sleeps 6, features a fully equipped kitchen with dishwasher, central AC, high-speed internet (300 Mbps), solar panels, and a private garden with deck.
Beautiful Sunsets And Saltwater Views From Every Room - Chatham, MA
Chatham, MA
08/15 – 08/22
$3240/nighttotal: $22680 (7 )

Beautiful Sunsets And Saltwater Views From Every Room

5 10
apartment , Chatham
This luxurious North Chatham vacation home boasts unparalleled waterfront views of Nauset Beach, Bassing Harbor, and Pleasant Bay, offering convenient access to Chatham Lighthouse Beach and the Chatham Windmill.
The 4,500-square-foot Cape Cod-style house features five bedrooms, four and a half bathrooms, sleeps twelve guests, and includes a chef's kitchen, expansive deck, private beach access, and central air conditioning.
Pleasant Bay Village Resort - Chatham, MA
9.6 407 reviews
Chatham, MA
06/18 – 06/27
$807/nighttotal: $7263 (9 )

Pleasant Bay Village Resort

2 2
resort , Chatham
The Pleasant Bay Village Resort is located in Chatham, Massachusetts, just 2.5 miles from the Chatham Railroad Museum and an 8-minute drive from the Chatham Lighthouse. This 4-star resort has received excellent user ratings for its location, cleanliness, and overall experience.
The resort offers spacious rooms with comfortable furnishings, floral décor, cable TV, a fridge, and a work desk. Guests can enjoy a variety of amenities and activities, including a seasonal outdoor pool, a hot tub, a game room, a children's playground, ping-pong, laundry facilities, and a restaurant.
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