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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

Walk 2beach, Pool, Hot Tub, Gameroom, Petsok - Chatham, MA
No reviews

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

house, Chatham
This substantial holiday let in Chatham is located a short walk from the beach, approximately 1.9 kilometres from Harding Beach and within driving distance of Nauset Lighthouse (25.7 kilometres) and the Cape Cod National Seashore (29 kilometres).
This pet-friendly property offers 3600 square meters of living space with 4 bedrooms and 4 bathrooms, accommodating up to 19 guests, and features a private swimming pool, hot tub, and a dedicated games room.
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok - Chatham, MA
10 15 reviews

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

apartment, Chatham
This four-bedroom apartment in Chatham is situated just a short walk from Hardings Beach, offering easy access to the beautiful coastline.
The 334.45 square metre property boasts a private pool and hot tub, a game room, a movie room, and an outdoor kitchen with a fire pit area, providing ample space and entertainment options for up to 10 guests.
Luxury Home With Pool, Hot Tub & Water View - Chatham, MA
10 3 reviews

Luxury Home With Pool, Hot Tub & Water View

apartment, Chatham
This five-bedroom, six-bathroom waterside residence in North Chatham offers prime waterfront positioning, just 990 metres from the Chatham Shark Centre and 1.2 kilometres from the Chatham Marconi Maritime Centre, providing convenient access to local maritime attractions and nearby beaches.
Spanning 361 square metres, this spacious holiday home accommodates up to 12 guests and features a well-equipped kitchen, air conditioning, Wi-Fi, a garden, a communal swimming pool, a hot tub, and on-site parking, ideal for exploring the area on foot.
The Barn At Chatham Oaks - Chatham, MA
9.6 12 reviews

The Barn At Chatham Oaks

apartment, Chatham
This Chatham holiday home is situated near the sea, less than 2km from the Chatham Chamber of Commerce and Cape Cod beaches, with Ridgevale Beach and Cockle Cove Beach also within 3km.
This 372 square metre property boasts seven bedrooms, five bathrooms, sleeps sixteen guests, and includes a private pool, sauna, and fully equipped kitchen; free Wi-Fi is also provided.

Best family friendly Chatham, MA lodging

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

Charming Coastal Hideaway With Outdoor Shower - Inviting Summer Oasis - Chatham, MA
10 7 reviews

Charming Coastal Hideaway With Outdoor Shower - Inviting Summer Oasis

house, Chatham
This detached property in Chatham is situated 965 metres from Cockle Cove Beach on Nantucket Sound and 483 metres from the Cape Cod Rail Trail.
This family-friendly holiday home for eight guests features three bedrooms, two bathrooms, air conditioning, WiFi, a screened-in porch, and includes daily free tickets to local attractions through Xplorie, such as whale watching and bike rentals.
Updated 4br Close To Downtown Chatham, Beaches, Bike Path & Tennis Pickleball - Chatham, MA
10 15 reviews

Updated 4br Close To Downtown Chatham, Beaches, Bike Path & Tennis Pickleball

apartment, Chatham
This Chatham apartment, a renovated house in the town centre, offers direct access to the Cape Cod Rail Trail and is within walking distance of restaurants such as Del Mar and shops, plus Oyster Pond.
The 141 square metre property sleeps eight, boasting three bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, a private garden with outdoor shower (seasonal), and parking.
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.
Beachfront Charmer! Newly Renovated. - Chatham, MA
9.9 117 reviews

Beachfront Charmer! Newly Renovated.

apartment, Chatham
This Chatham holiday home, a short 0.09km stroll from Little Beach and a 0.8km walk from Chatham Lighthouse and Lighthouse Beach, offers easy access to the town centre (1.6km away).
Sleeping seven guests across three bedrooms and two bathrooms, the property boasts a modern kitchen with a dishwasher and Keurig coffee maker, two living areas (including a 65" TV), a private balcony, gas grill, outdoor shower, and ample parking.

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

Classic Home With Deck, Patio & Yard - Walk To Cockle Cove & Forest Beaches - Chatham, MA
9.8 55 reviews

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

apartment, Chatham
This South Chatham flat is situated a block from Main Street and 750 metres from Forest Beach, offering proximity to local attractions.
This 138 square metre dwelling accommodates six guests with three bedrooms and two bathrooms, featuring a fully equipped kitchen, free WiFi, a fenced yard, private deck, outdoor shower, and gas grill.
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 the beautiful Cape Cod Beaches and the town centre. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The 169 square metre home comfortably sleeps eight guests in four bedrooms and two bathrooms. Guests can enjoy a fully equipped kitchen, a garden, and parking, along with a variety of other amenities including air conditioning, internet access, and a washing machine.
Spacious 4br House In Perfect Chatham With Ac - Chatham, MA
No reviews

Spacious 4br House In Perfect Chatham With Ac

apartment, Chatham
This detached house in Chatham provides peaceful lake access and is located 2.4 kilometres from Chatham Village's Main Street, with ocean beaches a short drive away.
This family-friendly property accommodates up to 8 guests in four bedrooms, featuring a vaulted sunroom with a bar, a large wooden deck, a private wooded garden, and deeded access to a private boat ramp for immediate lake enjoyment.
Waterfront Escape, Game Room, Dog Friendly! - Chatham, MA
No reviews

Waterfront Escape, Game Room, Dog Friendly!

apartment, Chatham
This waterfront residence in West Chatham offers direct sea access and panoramic water views, situated approximately 1.0 kilometre from Harding's Beach and Ridgevale Beach, and a short drive to Chatham's amenities.
This spacious 465 square metre holiday home features 6 bedrooms and 4 bathrooms accommodating up to 12 guests, with a basement games room, outdoor dining deck, wood fire pit, and is dog-friendly.

Best Chatham, MA accommodations with a kitchen

Quaint Chatham Home W/beautiful Backyard & Furnished Multi-level Deck, Dogs Ok - Chatham, MA
9.6 105 reviews

Quaint Chatham Home W/beautiful Backyard & Furnished Multi-level Deck, Dogs Ok

apartment, Chatham
This Chatham holiday flat is located approximately 1.6 kilometres from Hardings Beach and just over 3.2 kilometres east of Chatham's shops and restaurants, with the Barn Hill boat launch 400 metres away.
This 91 square metre apartment accommodates up to six guests, featuring two bedrooms, one bathroom, a gas fireplace, a well-equipped kitchen, and a landscaped garden with a multi-level deck, plus beach gear available for use.
Chit-chat Cottage On White Pond, Near Dt/beaches. - Chatham, MA
9.9 77 reviews

Chit-chat Cottage On White Pond, Near Dt/beaches.

apartment, Chatham
This Chatham waterfront holiday home is situated within 3.2 kilometres of the Monomoy Theatre, Chatham Drama Guild, Veterans Field, Chatham Railroad Museum, and Mayo House.
The two-bedroom self-catering property sleeps four, boasts a private garden, patio, spa, and free Wi-Fi, offering excellent proximity to Chatham's attractions and waterside activities.
Updated Beach House Deck Outdoor Shower! - Chatham, MA
9.8 8 reviews

Updated Beach House Deck Outdoor Shower!

house, Chatham
This Chatham beach house, less than 1 km from Forest Beach and 3 km from Ridgevale Beach, offers easy access to Cape Cod attractions such as Nauset Lighthouse (24 km away).
The 92 square metre property sleeps six, boasting two bedrooms, one bathroom, a fully equipped kitchen with fridge and dishwasher, free Wi-Fi, air conditioning, and parking; an outdoor shower is perfect after a day at the beach.
Riviera Sunset - Chatham, MA
9.2 7 reviews

Riviera Sunset

house, Chatham
The Riviera Sunset is a beachfront apartment in Chatham, located a short walk from Chatham Lighthouse Beach and a drive from Cape Cod National Seashore.
The 52 square metre apartment features two living rooms, a fully equipped kitchen, a private entrance, and can accommodate up to seven guests.
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