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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

Exclusive Harwich Haven: Pool, Spa And More Rpam068 - Chatham, MA
10 7 reviews

Exclusive Harwich Haven: Pool, Spa And More Rpam068

apartment, Harwich
This spacious four-bedroom holiday home is located just a short drive from the beautiful Cape Cod Beaches and the popular Captains Golf Club, making it an ideal base for exploring the area. The surrounding area is known for its peaceful atmosphere and stunning natural beauty.
The property offers ample space for families and groups, with a capacity of up to 10 guests. It features a fully equipped kitchen, a comfortable living area, and a private pool and hot tub, ensuring a relaxing and enjoyable stay.
Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks - Chatham, MA
10 6 reviews

Gorgeous Luxury Waterfront Retreat: Pool, Tennis, Pickleball, Kayaks

apartment, Chatham
This townhome offers a prime waterfront location in Chatham, Massachusetts, on 17.5 acres overlooking Oyster Pond, providing direct access to Oyster River, Stage Harbor, Nantucket Sound, South Beach, Monomoy Island, and the Atlantic Ocean via a private dock, with downtown Chatham's shops and restaurants just a short walk away.
This spacious 209 square meter apartment comfortably accommodates up to 8 guests across 2 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, air conditioning, a swimming pool, terrace, garden, parking, and access to tennis courts and shuffleboard within the Oyster Pond Condominium Complex.
229 M² House ∙ 4 Bedrooms ∙ 8 Guests - Chatham, MA
No reviews

229 M² House ∙ 4 Bedrooms ∙ 8 Guests

house, Harwich
This Harwich holiday home is located within easy reach of Harwich Port's shops and restaurants, and approximately 2.9 kilometres from Jacknife Beach.
This 228 square metre dwelling accommodates up to eight guests and includes four bedrooms, two bathrooms, a kitchen with a fridge, microwave, and dishwasher, air conditioning, a private swimming pool, hot tub, and complimentary daily tickets to local attractions through Xplorie, such as Island Cruises and Whale Watch tours.
Ocean Edge Resort Ground-floor Condo With Access To Pools, Hot Tub, & Tennis - Chatham, MA
9.0 20 reviews

Ocean Edge Resort Ground-floor Condo With Access To Pools, Hot Tub, & Tennis

apartment, Brewster
This ground-floor condominium in Brewster, located within the Ocean Edge Resort, offers direct access to the 10-kilometre Cape Cod Rail Trail and is within 1 kilometre of ten Brewster Bay beaches, including Ellis Landing Beach.
This 88 square metre apartment sleeps six guests and features two bedrooms and two bathrooms, a full kitchen with stainless steel appliances, air conditioning, a private patio, and in-unit laundry, with resort amenities such as a swimming pool and hot tub available.

Best family friendly Chatham, MA lodging

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

Private Beach In Chatham - Sleeps 5 - Chatham, MA
9.8 134 reviews

Private Beach In Chatham - Sleeps 5

apartment, Chatham
This Chatham beachfront apartment offers direct access to a private beach, is less than 1.6km from Chatham town centre with its shops and restaurants, and a short walk from Chatham Lighthouse Beach and the Monomoy National Wildlife Refuge.
Sleeping five comfortably, this two-bedroom, one-bathroom property features a king-size bed, full-size bed, and twin bed, a fully equipped kitchen, keyless entry, Wi-Fi, two parking spaces, and access to an outdoor dining area with a Weber gas grill and an enclosed outdoor shower, plus a fitness centre.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.2 96 reviews

The Mansion At Ocean Edge Resort & Golf Club

manor house, Brewster
The Mansion at Ocean Edge, a resort in Brewster, offers direct beach access and is located 15.8 kilometres from Mayflower Beach and 1.2 kilometres from Ocean Dunes Golf Club.
This family-friendly resort provides an on-site spa, multiple dining options including a restaurant with garden views and a bar, a swimming pool, a fitness centre, and tennis courts, with complimentary parking available.
111 M² House ∙ 2 Bedrooms ∙ 4 Guests - Chatham, MA
10 2 reviews

111 M² House ∙ 2 Bedrooms ∙ 4 Guests

house, Chatham
This Chatham holiday home is situated near Schoolhouse Pond, a short drive (approximately 1.6km) from Hardings Beach, Chatham town centre, Coast Guard Beach, and the Cape Cod Rail Trail.
The 110 square metre property boasts a two-bedroom, two-bathroom layout sleeping four guests, includes a fully equipped kitchen, spa, garden, parking, and the Xplorie $750 attraction pass.
Four Shore: 
Walk To Town And Oyster Pond Beach - Chatham, MA
No reviews

Four Shore: Walk To Town And Oyster Pond Beach

apartment, Chatham
This spacious 4-bedroom, 4-bathroom residence, a former Greek Revival home built in 1904, is situated on the scenic Chatham Loop, offering convenient walking access to downtown Chatham's shops and eateries, as well as the child-friendly Oyster Pond Beach, with the harbour and Lighthouse Beach a short drive away.
The property accommodates up to 10 guests and features a well-equipped deck for outdoor dining, a garden for games, 10 beach chairs, an umbrella, a wagon, an outdoor shower, and a dedicated office, making it an ideal base for exploring the area.

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

Waterfront House On Bucks Creek Marsh With Deck, Dock, & Kayaks - Chatham, MA
9.2 47 reviews

Waterfront House On Bucks Creek Marsh With Deck, Dock, & Kayaks

apartment, Chatham
This luxurious waterside residence in West Chatham offers direct access to Bucks Creek Marsh and Nantucket Sound, with Harding's Beach just 500 meters away.
This impressive 291 square meter apartment sleeps up to six guests and boasts a chef's kitchen, a private dock with kayaks and rowboats, and an expansive mahogany deck perfect for enjoying sunset views over the water.
Steps To Oyster Pond Private Dock! - Chatham, MA
10 54 reviews

Steps To Oyster Pond Private Dock!

apartment, Chatham
This Chatham seaside property, less than 2km from Atwood House Museum, Chatham Windmill, and other local attractions, offers stunning ocean views.
The 254 square metre house sleeps eight guests in three bedrooms and three bathrooms, boasting a fully equipped kitchen, terrace, garden, parking, and barbecue facilities.
Steps2beach &Rail Trail | Blueberry Pond Sanctuary - Chatham, MA
No reviews

Steps2beach &Rail Trail | Blueberry Pond Sanctuary

apartment, Brewster
This five-bedroom, three-bathroom detached house in Brewster offers immediate access to the Cape Cod Rail Trail, Nickerson State Park, and Blueberry Pond, with bay beaches such as Breakwater Beach and Paine's Creek just minutes away.
This property boasts a spacious 0.7-acre private garden with a fire pit and Adirondack chairs, a jacuzzi tub in the master en-suite, an outdoor shower, and an open-plan upper-level living, dining, and kitchen space with vaulted ceilings and a gas fireplace, accommodating up to six guests.
Beachside Harwich Port Apartment Near Town - Chatham, MA
No reviews

Beachside Harwich Port Apartment Near Town

apartment, Harwich
This flat is located in Harwich Port Village Landing, a two-minute walk from Bank Street Beach and a short stroll to Harwich Port's shops and restaurants.
This 72 square metre apartment accommodates up to four guests and features a modern, coastal-chic interior with a private covered deck offering sunrise views, complimentary linens, a washer/dryer, assigned parking, and daily free tickets to local attractions through Xplorie, including Island Cruises and Whale Watch.

Best Chatham, MA accommodations with a kitchen

Quaint Downtown Chatham Home - Chatham, MA
9.8 205 reviews

Quaint Downtown Chatham Home

apartment, Chatham
This charming 1851 vintage home is located on a private road in a downtown neighbourhood, just 800 metres from Lighthouse Beach and a short walk from the centre of Chatham. This family-friendly property has received excellent ratings for location, cleanliness, and overall experience.
The house has two bedrooms and one bathroom, accommodating up to five guests. It features a fully equipped kitchen, a spacious living and dining area, an enclosed sleeping porch with a twin day bed, and a garden with parking.
Newly Renovated Guest House Near The Beach! - Chatham, MA
10 17 reviews

Newly Renovated Guest House Near The Beach!

apartment, Harwich
This Harwich guesthouse is situated a short walk from the beaches and close to local shops and family-friendly attractions.
Sleeping up to seven guests, the property boasts three bedrooms with private TVs, a spacious living area, a modern bathroom, a fully equipped kitchen, and a peaceful patio; discreet owners reside separately.
Star Of The Sea Chatham Beach House - Chatham, MA
9.8 20 reviews

Star Of The Sea Chatham Beach House

apartment, Chatham
This South Chatham holiday home, situated on Main Street (Route 28), is 1.45 km from Cockle Cove Beach and a short drive from Chatham's town centre, offering easy access to restaurants, shops, and attractions such as The Squire and Chatham Bars Inn.
The newly renovated property sleeps up to 7 guests in 2 bedrooms and features an open-plan living/dining/kitchen area, a private backyard with a grill and outdoor games, ample parking, and direct access to the Cape Cod Rail Trail.
Kelley Lane - Cht- Kl161 - Chatham, MA
No reviews

Kelley Lane - Cht- Kl161

house, Chatham
This detached house in Chatham is located 2.9 kilometres from Oyster Pond Beach and offers convenient access to regional attractions such as Nauset Lighthouse (25.7 kilometres) and Wellfleet Bay Wildlife Sanctuary (27.3 kilometres).
This property boasts a floor area of 389 square meters, accommodating up to 19 guests across 4 bedrooms and 5 bathrooms, with amenities including air conditioning, WiFi, a fully equipped kitchen with a dishwasher and oven, a washing machine, and private parking, whilst also facilitating activities like cycling in the Chatham area.
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