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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.

Chatham Village - Lovely 2 Bedroom Apartment In The Antique Home - Chatham, MA
9.8 80 reviews

Chatham Village - Lovely 2 Bedroom Apartment In The Antique Home

apartment, Chatham
This Chatham apartment rental is centrally located, less than a mile from Mayo House and Cape Cod beaches, and within 15 minutes of the Chatham Windmill and Monomoy Theatre.
The two-bedroom, two-bathroom unit sleeps four guests and features a fully equipped kitchen, private patio, free WiFi, fireplace, shared garden with barbecue grills, and on-site parking.

Best family friendly Chatham, MA lodging

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

Chatham-walk To Ridgevale Beach, Pets Considered, Central Air, Bike Trail - Chatham, MA
9.6 55 reviews

Chatham-walk To Ridgevale Beach, Pets Considered, Central Air, Bike Trail

apartment, Chatham
This Chatham vacation rental is located near the coast, a short walk from Ridgevale Beach and Cape Cod Beaches, and within 2 miles of the Chatham Chamber of Commerce and Cockle Cove Beach. The house has received excellent user ratings, making it a popular choice for travelers.
This 3-bedroom home comfortably accommodates 9 guests. The property offers a range of amenities, including a fully equipped kitchen, air conditioning, a terrace or balcony, a garden, parking, and internet access.
New! 4br Fire Pit, Ping Pong, Movie Room - Chatham, MA
10 2 reviews

New! 4br Fire Pit, Ping Pong, Movie Room

apartment, Harwich
This four-bedroom, two-bathroom apartment in Harwich offers a secluded cul-de-sac setting, located a 10-minute walk from the Cape Cod Rail Trail and a 5-7 minute drive to Red River Beach and Bank Street Beach.
This 1590 sq ft home accommodates up to seven guests and features a movie room with foosball, a popcorn machine, a ping pong table in the garage, a back deck with a gas grill, an outdoor shower, a fire pit, and a dedicated nursery with baby amenities.
Downtown Chatham Gem  Walk To Beach, Shops, C.b.i, & Dining Family-friendly! - Chatham, MA
10 22 reviews

Downtown Chatham Gem Walk To Beach, Shops, C.b.i, & Dining Family-friendly!

apartment, Chatham
This five-bedroom Chatham rental is ideally located in downtown Chatham, a short walk from Main Street, Chatham Bars Beach, and the Chatham Orpheum Theater.
This 2,800-square-foot home boasts two living rooms, sleeps twelve guests comfortably, and includes a fully equipped kitchen, a screened porch, beach gear, and parking for four cars.
Dog-friendly Home W/yard, Deck, Free Wifi, New Gas Grill - Walk To The Beach - Chatham, MA
9.2 27 reviews

Dog-friendly Home W/yard, Deck, Free Wifi, New Gas Grill - Walk To The Beach

apartment, Chatham
This dog-friendly Cape Cod cottage in South Chatham offers a quintessential summer experience, located less than a mile from Forest Beach and four miles from downtown Chatham's shops and restaurants.
This 1100 square foot, single-level home comfortably accommodates up to five guests with two bedrooms, one bathroom, a full kitchen, and an expansive yard with an outdoor deck, ideal for enjoying nearby biking, fishing, and golf.

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.

Inviting Pool And Close To Beach - Charming Coastal Getaway - Chatham, MA
No reviews

Inviting Pool And Close To Beach - Charming Coastal Getaway

house, Harwich
This Harwich rental house is located on a hill, offering 2,640 feet of access to Jackknife Beach and 0.4 miles to Wequassett Resort, with downtown Chatham shops and restaurants 3 miles away.
This family-friendly, pet-friendly home accommodates 10 guests in 5 bedrooms and 3.5 bathrooms, featuring central air conditioning, a private outdoor pool, an air hockey table, a ping pong table, and WiFi.
Enjoy Your Own Private Pool In Chatham! (2252) - Chatham, MA
9.6 4 reviews

Enjoy Your Own Private Pool In Chatham! (2252)

apartment, Chatham
This South Chatham apartment is a short drive from the beautiful beaches of Cape Cod, offering easy access to the region's natural beauty and attractions.
The 4-bedroom, 3-bathroom home features two separate living quarters, a private pool, two decks, a gas grill, and a spacious yard for outdoor enjoyment.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2643 reviews

The Mansion At Ocean Edge Resort & Golf Club

resort, Brewster
The Mansion at Ocean Edge Resort and Golf Club is located in Brewster, a short drive from the Cape Cod Museum of Natural History and the Wellfleet Drive-In Theater & Cinemas. The resort has excellent ratings for location, cleanliness, and overall experience.
The resort offers spacious villas with full kitchens and living rooms, ideal for families or groups. Guests can enjoy a private beach, indoor and outdoor pools, a golf course, tennis courts, a kids' club, multiple dining options, and a fitness center.
The Barn At Chatham Oaks - Chatham, MA
9.8 11 reviews

The Barn At Chatham Oaks

apartment, Chatham
This Chatham vacation home is located near the ocean, less than 1.2 miles from the Chatham Chamber of Commerce and Cape Cod beaches, and within 1.9 miles of Ridgevale Beach and Cockle Cove Beach.
This 4,000-square-foot house boasts seven bedrooms, five bathrooms, and accommodates up to 16 guests, featuring a private pool, sauna, and fully equipped kitchen with a dishwasher; outdoor amenities include a terrace, garden, and barbecue grills.

Best Chatham, MA accommodation with a kitchen

145 M² House ∙ 4 Bedrooms ∙ 10 Guests - Chatham, MA
10 3 reviews

145 M² House ∙ 4 Bedrooms ∙ 10 Guests

house, Chatham
Poppy's Place, a four-bedroom Chatham house rental, is located in a quiet neighborhood, 0.25 miles from Goose Pond and 2.6 miles from Chatham's town center, offering easy access to beaches like Jackknife Harbor and the bike path.
This 1,560-square-foot, three-level home sleeps up to 10 guests and includes a fully equipped kitchen, three bathrooms, a private patio, and a fenced backyard; plus, enjoy a Guest Welcome Bag and $750 in Xplorie tickets to local attractions.
"Chatham Up - Chatham, MA
9.0 44 reviews

"Chatham Up

apartment, Chatham
This charming vacation rental in North Chatham is conveniently located just a short walk from Veteran's Field, home to the Chatham A's Baseball team, and a mile from Oyster Pond. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The 1190 square foot home comfortably accommodates up to five guests in its two bedrooms and one bathroom. Enjoy the convenience of a fully equipped kitchen, air conditioning, a spacious living area, and a large side yard perfect for outdoor games, all while taking advantage of the nearby beach and local attractions.
Beachside Bliss: Dog Friendly Breezy Stay - Chatham, MA
No reviews

Beachside Bliss: Dog Friendly Breezy Stay

house, Chatham
This South Chatham vacation rental is a short walk from Cockle Cove Beach and within 15-17 miles of attractions like the Nauset Lighthouse and Wellfleet Bay Wildlife Sanctuary.
The 2,300-square-foot house features one bedroom, three bathrooms, and can accommodate up to 15 guests, offering amenities such as a fully equipped kitchen, air conditioning, cable TV, and Wi-Fi.
Spacious W Large Outdoor Area Fire Pit - Chatham, MA
8.5 2 reviews

Spacious W Large Outdoor Area Fire Pit

house, Chatham
This 2000 sq ft house is located in Chatham, 1.3 miles from Oyster Pond Beach, and offers convenient access to Wellfleet Bay Wildlife Sanctuary and Cape Cod National Seashore.
This home features four bedrooms, two bathrooms, a fully equipped kitchen, air conditioning, internet, and a large outdoor area with a fire pit, accommodating up to 15 guests with free private parking.

Best Chatham, MA accommodation with a balcony

West-facing Pure Waterfront Home In Orleans, Overlooking Arey's Pond - Chatham, MA
9.4 24 reviews

West-facing Pure Waterfront Home In Orleans, Overlooking Arey's Pond

apartment, Orleans
Walk To Pleasant St Beach! - Chatham, MA
10 1 review

Walk To Pleasant St Beach!

cottage, Chatham
Beautiful Home W/ Artistic Flair! - Chatham, MA
9.8 38 reviews

Beautiful Home W/ Artistic Flair!

apartment, Chatham
Pool, Half Mile To Beach! - Chatham, MA
10 2 reviews

Pool, Half Mile To Beach!

apartment, Harwich

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.

Chatham Condo With Private Entrance - Chatham, MA
9.9 72 reviews

Chatham Condo With Private Entrance

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.

Main Street Chatham Village Downtown-new Listing! - Chatham, MA
9.8 82 reviews

Main Street Chatham Village Downtown-new Listing!

house, Chatham
Chatham Escape *Pet Friendly* - Chatham, MA
10 4 reviews

Chatham Escape *Pet Friendly*

apartment, Chatham
Walk To Schoolhouse Pond! - Chatham, MA
No reviews

Walk To Schoolhouse Pond!

apartment, Chatham
7-br Retreat: Pool, Hot Tub, Sauna, Barn - Chatham, MA
9.9 77 reviews

7-br Retreat: Pool, Hot Tub, Sauna, Barn

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.

Chatham Family Vacation - Chatham, MA
9.9 47 reviews

Chatham Family Vacation

apartment, Chatham
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