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Chatham, MA place to stay
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1503 Lodgings in Chatham, MA

Best Chatham, MA lodging with a pool

Among the 1503 accommodations in Chatham, MA, here are the 4 best ones with a pool

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 situated in Harwich, a short drive from the centre of town and close to Cape Cod National Golf Center and the stunning Cape Cod National Seashore. It has received excellent ratings for both its location and overall experience, with guests praising its cleanliness and friendly service.
The resort offers a range of accommodation options, from spacious rooms to luxurious suites, all featuring comfortable sitting areas and private decks or patios. Guests can enjoy a variety of amenities, including a swimming pool, hot tub, fitness centre, tennis court, and a restaurant serving delicious seafood and American classics.
Riviera Sunset - Chatham, MA
No reviews

Riviera Sunset

house, Chatham
Vacation house rental. This accommodation is located in Chatham.
Facilities and services: a fridge, a barbecue and a dish washer. This house also has air conditioning!
Stones Throw: 052-cs  Alluring Chatham In-town Home With Pool, Walk To It All - Chatham, MA
10 5 reviews

Stones Throw: 052-cs Alluring Chatham In-town Home With Pool, Walk To It All

apartment, Chatham
This in-town Chatham residence is situated 0.4 kilometres from Oyster Pond Beach and a 5-minute walk from Main Street's shops and restaurants.
This 260 square metre apartment offers accommodation for 10 guests, featuring four bedrooms, three bathrooms, a well-equipped kitchen with a dishwasher, air conditioning, a swimming pool, hot tub, and a game room with foosball and air hockey.
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 holiday home, near Ridgevale Beach (1.8 km) and Cockle Cove Beach (2.4 km), offers easy coastal access.
This seven-bedroom property boasts 372 square metres of floor space, accommodating up to 20 guests and featuring a private pool, spa, and fully equipped kitchen; nearby attractions include Cape Cod National Seashore (37 km) and Nauset Lighthouse (24 km).

Best family friendly Chatham, MA lodging

Among the 1503 accommodations in Chatham, MA, here are the 4 best for families

Slate House - A Modern Waterfront Getaway - Chatham, MA
9.9 320 reviews

Slate House - A Modern Waterfront Getaway

apartment, Chatham
This Chatham apartment is located in a peaceful private oasis just a short walk from a dog-friendly beach and a short drive from other beaches, offering a secluded escape from the hustle and bustle. It has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious apartment is perfect for families and groups, with three bedrooms and two bathrooms, accommodating up to nine guests. It boasts a modern kitchen with a fridge, microwave, and dishwasher, along with a Jacuzzi, a garden, and parking. Enjoy the beautiful waterfront views from the screened-in lounge area, complete with a fire pit for cozy evenings.
Chatham-walk To Town/beach-multi Family Friendly - Chatham, MA
10 59 reviews

Chatham-walk To Town/beach-multi Family Friendly

apartment, Chatham
This spacious holiday home is located in central Chatham, less than 1.6 km from Atwood House Museum and Cape Cod Beaches, as well as Mayo House and Gallery Antonia. The property has received excellent reviews from previous guests.
This five-bedroom property offers 446 square metres of living space and can accommodate up to 12 guests. The house provides a range of amenities, including a fully equipped kitchen, a terrace, a garden, and free Wi-Fi.
Stunning Outdoor Space And Relaxing Den - Charming Coastal Haven - Chatham, MA
No reviews

Stunning Outdoor Space And Relaxing Den - Charming Coastal Haven

house, Chatham
This detached dwelling is situated in the sought-after Cockle Cove district, a mere 966 metres from Cockle Cove Beach and 483 metres from the Cape Cod Rail Trail, with Harwich and Chatham town centres a short drive away.
This family-friendly property accommodates up to eight guests with three bedrooms and two bathrooms, featuring central air conditioning, a well-equipped kitchen, two living areas, a gas grill, an outdoor shower, and includes a complimentary Xplorie package offering daily tickets to local attractions.
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 Cape Cod property is situated in Chatham, a mere 965 metres from Schoolhouse Pond, with Hardings Beach and the town centre a short drive away.
This two-bedroom, two-bathroom bungalow accommodates up to four guests and offers amenities including air conditioning, Wi-Fi, a recently renovated kitchen, a TV room with a sofa bed, an outdoor shower, and complimentary daily tickets to local attractions through Xplorie, such as Island Cruises and Whale Watch.

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 landmark with a rich history. The Chatham Historical Society is another must-visit for its exhibits on the town's past. And if you're looking for a scenic walk, the Chatham Bars Inn is a beautiful spot right on the beach.
  • How can travelers reach Chatham, MA?

    The easiest way to get to Chatham is by car. It's a scenic drive from Boston, about 2 hours. If you're flying in, the nearest airport is in Hyannis, about 40 minutes away. There are also buses that run from Boston, but they take a bit longer.
  • What outdoor activities can visitors enjoy in and around Chatham, MA?

    Chatham is a paradise for outdoor enthusiasts! You can spend your days swimming, sunbathing, or surfing at Chatham Beach. If you're feeling adventurous, try kayaking or paddleboarding in Pleasant Bay. Or, hike the trails at the Cape Cod National Seashore for breathtaking views.
  • When is the ideal time to plan a trip to Chatham, MA?

    The best time to visit Chatham is during the summer months, from June to August, when the weather is warm and sunny. You'll be able to enjoy the beaches and outdoor activities to the fullest. But if you prefer a quieter experience, spring or autumn can be lovely too, with beautiful foliage and fewer crowds.
  • What are the best walking or cycling routes in Chatham, MA?

    For a leisurely walk, try the Chatham Rail Trail, a paved path that follows the old railroad line. It's great for a stroll or a bike ride. You can also explore the charming streets of Chatham Village, stopping at the shops and restaurants along the way.
  • What nearby towns or cities can be explored from Chatham, MA?

    Chatham is a great base for exploring the Cape. You can easily drive to nearby towns like Harwich Port, known for its beautiful harbour, or Provincetown, a vibrant arts community at the tip of the Cape. For a day trip, consider visiting the historic town of Plymouth, about an hour away.
  • What amenities can travelers expect from accommodations in Chatham, MA?

    Chatham offers a wide range of accommodation options, from charming bed and breakfasts to luxurious hotels. Many places offer amenities like swimming pools, fitness centres, and restaurants. Some even have private beaches, perfect for a relaxing getaway.

Popular destinations

Best Chatham, MA accommodations with a balcony

Home Near Beach & Tennis/basketball Court With Firepit, Grill, & Patio - Chatham, MA
10 1 review

Home Near Beach & Tennis/basketball Court With Firepit, Grill, & Patio

apartment, Chatham
This South Chatham holiday home is situated on a private lane, just 530 metres from Forest Beach and near public tennis and basketball courts.
This 154 square metre apartment offers accommodation for up to six guests, featuring two bedrooms, three bathrooms, a well-equipped kitchen with a dishwasher, air conditioning, a terrace/balcony, and a garden with a firepit and grilling area.
Beach Chic Chatham Retreat-mins Walk Private Beach - Chatham, MA
10 134 reviews

Beach Chic Chatham Retreat-mins Walk Private Beach

apartment, Chatham
This family-friendly holiday home is located in South Chatham, a short 15-minute walk from the Chatham Chamber of Commerce and Cape Cod Beaches. The property has received excellent ratings for location, cleanliness, and user experience.
The spacious 139 square metre property can accommodate up to 10 guests. This self-catering accommodation offers a range of amenities including a swimming pool, tennis court, spa, and water park, making it ideal for a fun-filled family holiday.
Cape Springs Cottage - Chatham, MA
No reviews

Cape Springs Cottage

house, Chatham
Vacation house to rent. You will be in Chatham.
Facilities and services include a fridge, a washing machine and a terrace. This house in Chatham also has air conditioning!
Seaside Condo With Patio, Beach Access, Loft, Board Games, Gas Grill, & Firepit - Chatham, MA
10 1 review

Seaside Condo With Patio, Beach Access, Loft, Board Games, Gas Grill, & Firepit

apartment, Chatham
This Chatham flat provides direct access to Lighthouse Beach and is a short walk from Chatham Harbour and Chatham Lighthouse, offering a historical perspective.
This 52 square meter apartment accommodates up to four guests, featuring one bedroom, a full kitchen, air conditioning, a loft accessible by ladder, an outdoor shower, and a patio area, with board games and books provided.

Best Chatham, MA accommodations with a kitchen

Spacious W Large Outdoor Area Fire Pit - Chatham, MA
8.5 2 reviews

Spacious W Large Outdoor Area Fire Pit

house, Chatham
This spacious Chatham holiday home, situated 2.1km from Oyster Pond Beach and within easy reach of attractions such as the Nauset Lighthouse (22.5km), Truro Historical Museum (45km), and Sandwich Glass Museum (48km), offers a convenient base for exploring Cape Cod. This 186 square metre property boasts a four-bedroom, two-bathroom layout, comfortably sleeping up to 15 guests and featuring a fully equipped kitchen, garden, parking, and air conditioning.
The Boarding House. Steps From Ice Cream Shop - Chatham, MA
10 76 reviews

The Boarding House. Steps From Ice Cream Shop

apartment, Chatham
This charming house is situated just 1.6km from the Chatham Chamber of Commerce and Cape Cod Beaches, offering a prime location for exploring the area. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The property spans 149 square metres and comfortably accommodates up to 8 guests across its four bedrooms. Guests can enjoy a range of amenities, including a private garden, barbecue grills, and a fully equipped kitchen, making it perfect for families and groups seeking a relaxing and enjoyable stay.
Spacious Dog-friendly Retreat In Chatham - Chatham, MA
10 1 review

Spacious Dog-friendly Retreat In Chatham

apartment, Chatham
This dog-friendly three-bedroom, three-bathroom flat in Chatham offers a secluded setting within a natural environment, with a daily Xplorie offer including Island Cruises, Whale Watch, Bike Rentals, and Whydah Pirate Museum admission worth £600.
This accommodation includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and outdoor shower, plus complimentary use of bikes and kayak life vests and paddles for exploring local waterways.
Hot Tub, Fenced Yard & Dog Friendly - Chatham, MA
9.9 84 reviews

Hot Tub, Fenced Yard & Dog Friendly

apartment, Chatham
This charming house is situated near the sea in Chatham, just a short walk from the Chatham Shark Center and Caleb Nickerson House, and within 3 kilometres of Cape Cod Beaches and Chatham Fish Pier. It has received excellent ratings for its location, cleanliness, and overall user experience.
The house offers 4 bedrooms and 2 bathrooms, with a floor area of 185 square metres. Enjoy modern conveniences like a coffee/tea maker, TV, and a fully equipped kitchen, as well as a garden, terrace, and barbecue grills for al fresco dining and relaxation.
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