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Chatham, MA accommodations
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1503 Lodgings in Chatham, MA

Find the Best Seaside Lodgings in Chatham, MA

Plan a refreshing beach-town holiday at these seaside accommodations in Chatham, MA, located just a short distance from popular coastal attractions.

Cape Cod Classic Cottage Near Forest Beach - Chatham, MA
9.9 196 reviews

Cape Cod Classic Cottage Near Forest Beach

apartment, Chatham
This two-bedroom cottage is situated in a peaceful Chatham neighborhood, just a short walk from Forest Beach and a quick drive to downtown Chatham.
The cottage boasts a fully renovated interior with modern amenities, including a gas stove, quartz countertops, central AC, a large walk-in shower, a 50-inch Samsung Frame TV with streaming services, and a backyard with a deck, hammock, and EV charging.

Best family friendly Chatham, MA lodging

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

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.
Ping-pong & Backyard: Spacious Chatham Retreat - Chatham, MA
No reviews

Ping-pong & Backyard: Spacious Chatham Retreat

house, Chatham
Vacation rental. Your accommodation will be based in Chatham.
Services and facilities include a barbecue, a kitchen and a fridge. Take advantage of the air conditioning in this house!
New 3 Bdrm/3b Near Jackknife Beach/wequassett/gameroom - Chatham, MA
10 2 reviews

New 3 Bdrm/3b Near Jackknife Beach/wequassett/gameroom

apartment, Chatham
This 3-bedroom house in Riverbay Estates, Chatham, is located 0.9 miles from Jackknife Cove Beach and 1.8 miles from Wequassett Resort, with downtown Chatham and Lighthouse Beach also a few miles away.
This 2400 square foot home accommodates up to 8 guests and features a chef's kitchen, a finished basement game room with pool and ping pong, a patio with a gas fire pit, and outdoor shower, with Wi-Fi and central air conditioning for comfort.
Serene Chatham Cottage Minutes From Beach - Chatham, MA
9.9 95 reviews

Serene Chatham Cottage Minutes From Beach

apartment, Chatham
Cranberry Cottage, located in West Chatham, is a short walk from the village center, close to beaches like Ridgevale Beach and Harding's Beach, and offers easy access to the Cape Cod Rail Trail and Chatham Airport.
This two-bedroom, one-bathroom home sleeps five, features a renovated kitchen opening to a private deck with a gas grill, and includes amenities such as a pack 'n play, high chair, beach toys, high-speed Wi-Fi, and a washer/dryer.

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.

Popular destinations

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.

The Gables: 364-c  Chatham Resort Style Estate With Heated Pool, Close To Everything - Chatham, MA
10 17 reviews

The Gables: 364-c Chatham Resort Style Estate With Heated Pool, Close To Everything

apartment, Chatham
This Chatham resort is located just a short walk from Main Street and Chatham Village, making it easy to explore the charming shops, restaurants, and attractions of the area. The resort has received excellent ratings from previous guests, highlighting its quality and appeal.
This 8-bedroom home comfortably sleeps 16 guests and features a spacious 4,290 square feet of living space. The home is equipped with a range of amenities, including a heated pool, hot tub, fire pit, outdoor kitchen, and multiple lounge areas, providing everything you need for a relaxing and enjoyable vacation.
Wequassett Resort And Golf Club - Chatham, MA
9.3 369 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.
Relaxing Fairway Escape With Resort Pools, Club Access, & Steps To Arbor Pool - Chatham, MA
10 1 review

Relaxing Fairway Escape With Resort Pools, Club Access, & Steps To Arbor Pool

apartment, Brewster
This 1500 sq ft condo is located on the 9th fairway of Ocean Edge Resort in Brewster, MA, offering golf course views and convenient shuttle service to Crosby Landing Beach, with easy access to local shops, restaurants, and the Cape Cod Rail Trail.
This family-friendly unit features 3 bedrooms, 2 bathrooms, cathedral ceilings, private decks, and onsite amenities like a Lego table, puzzles, and board games, with optional Ocean Edge Resort passes available for pools, hot tubs, and fitness facilities.
Luxury Home W/ Salt Water Pool Overlooking Ocean - Chatham, MA
10 32 reviews

Luxury Home W/ Salt Water Pool Overlooking Ocean

apartment, Chatham
This luxurious 4-bedroom, 5-bathroom Chatham rental home boasts breathtaking views of Buck's Creek and Nantucket Sound, offering easy access to Chatham's beaches, shops, and restaurants.
This fully renovated Cape Cod property features a chef's kitchen with a massive 12-foot eat-in island, a spacious cathedral-ceiling living room, and accommodates up to 10 guests, complete with a swimming pool, Jacuzzi, and private parking.

Best Chatham, MA accommodation with a kitchen

Large Home W Fire Pit And Dogs Welcome - Chatham, MA
8.5 4 reviews

Large Home W Fire Pit And Dogs Welcome

house, Chatham
This spacious Chatham house, located near Wellfleet Bay Wildlife Sanctuary (19 miles), Cape Cod National Seashore (21 miles), and Nauset Lighthouse (13 miles), offers easy access to popular Cape Cod attractions.
This 1770-square-foot home features a 4-bedroom layout, accommodating up to 19 guests, complete with a fully equipped kitchen, Wi-Fi, a private garden, fire pit, and pet-friendly amenities.
Chatham Village - Adorable Studio Apartment In Antique Home - Chatham, MA
9.4 100 reviews

Chatham Village - Adorable Studio Apartment In Antique Home

studio, Chatham
This Chatham apartment rental is conveniently located less than a mile from Mayo House and Cape Cod beaches, and within 15 minutes of the Chatham Windmill and Atwood House Museum.
The one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, in-unit laundry, a terrace, free Wi-Fi, a smart TV, air conditioning, parking, and access to a spa.
Quaint Chatham Getaway - Chatham, MA
9.8 32 reviews

Quaint Chatham Getaway

apartment, Chatham
This two-bedroom, one-bathroom apartment is located in a quiet area of lower Cape Cod, close to the Cape Cod Rail Trail and a short drive from Chatham beaches. The apartment features a spacious yard and deck, an outdoor shower, and a recently updated kitchen and bathroom, perfect for families or couples seeking a peaceful retreat.
Two Bedroom Condo Close To Beach - Chatham, MA
9.9 66 reviews

Two Bedroom Condo Close To Beach

apartment, Chatham
This two-story condo in West Chatham Village offers a unique layout, is a 15-minute walk from Ridgevale Beach, and is near Marion's Pie and the Cape Cod Rail Trail.
This Chatham vacation rental sleeps five, features two bedrooms and two bathrooms, a fully equipped kitchen with dishwasher, two assigned parking spots, upper and lower decks, an enclosed outdoor shower, and a grill.

Best Chatham, MA accommodation with a balcony

Luxury Chatham Escape W/ Stunning Waterfront Views - Chatham, MA
10 3 reviews

Luxury Chatham Escape W/ Stunning Waterfront Views

apartment, Chatham
Stroll Chatham's Historic Downtown / Shops, Dining, Galleries, Etc. - Chatham, MA
8.0 1 review

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

apartment, Chatham
Families, Enjoy Harwich, Pool, Large Hot Tub & Ac - Chatham, MA
No reviews

Families, Enjoy Harwich, Pool, Large Hot Tub & Ac

house, Harwich
Sophisticated Chatham Oasis With Pool & Spa Rpam062 - Chatham, MA
10 9 reviews

Sophisticated Chatham Oasis With Pool & Spa Rpam062

apartment, Chatham

Popular Luxury Lodgings in Chatham, MA

A coastal luxury lodging in Chatham, MA sets a wonderful tone for your trip, with 5-star comfort and premium views.

Breathtaking Riverfront Home With A Lovely Deck, Close To Beach - Dogs Ok - Chatham, MA
10 1 review

Breathtaking Riverfront Home With A Lovely Deck, Close To Beach - Dogs Ok

apartment, Chatham

Check Out Pet-Friendly Lodgings in Chatham, MA

A quality pet-friendly lodging in Chatham, MA means dog-friendly beaches and outdoor washing facilities are always part of the package.

Sarah-n-dipity: Cozy Cottage Near Ridgevale Beach - Chatham, MA
9.4 3 reviews

Sarah-n-dipity: Cozy Cottage Near Ridgevale Beach

cottage, Chatham
Ping-pong & Backyard: Spacious Chatham Retreat - Chatham, MA
10 2 reviews

Ping-pong & Backyard: Spacious Chatham Retreat

house, Chatham
Central Ac Close To Beach Dog Friendly! - Chatham, MA
9.9 91 reviews

Central Ac Close To Beach Dog Friendly!

apartment, Chatham
Summer Catch Lovely Updated Chatham Village Home - Chatham, MA
10 15 reviews

Summer Catch Lovely Updated Chatham Village Home

apartment, Chatham

Compare Accommodations with On-Site Dining in Chatham, MA

An on-site restaurant at your lodging in Chatham, MA ensures fresh local food and coastal dishes are available every evening.

Pond Front Home W Game Room Dog Friendly - Chatham, MA
9.2 6 reviews

Pond Front Home W Game Room Dog Friendly

house, Chatham
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