Compare accommodations in Chatham, MA from 100+ providers!

1503 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chatham, MA accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

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.

Spacious Harwich Home Near Round Cove (1116) - Chatham, MA
No reviews

Spacious Harwich Home Near Round Cove (1116)

apartment, Harwich
This Harwich condo is located a half mile from Round Cove on Pleasant Bay and close to Chatham and Orleans, situated in a quiet cul-de-sac.
This 3-bedroom, 2-bathroom rental accommodates up to 6 guests and features central air conditioning, a full kitchen, separate TV room, ample parking, and outdoor decks with an enclosed shower and gas grill.

Best family friendly Chatham, MA lodging

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

South Chatham Cottage Walk To Beaches, Dining, Tennis, Shops, Bike Path. - Chatham, MA
9.4 19 reviews

South Chatham Cottage Walk To Beaches, Dining, Tennis, Shops, Bike Path.

apartment, Chatham
This charming house in South Chatham is just a short walk from the Chatham Chamber of Commerce and Cape Cod Beaches, and a quick drive to Forest Beach and Cockle Cove Beach. Guests have consistently rated the property excellent.
The two-bedroom vacation home can comfortably accommodate four guests. The fully equipped kitchen, outdoor patio, and private garden offer everything needed for a relaxing and enjoyable stay in this peaceful and charming area.
Peaceful Retreat On Chilton Lane - Chatham, MA
No reviews

Peaceful Retreat On Chilton Lane

house, Brewster
This Brewster vacation home, located on Chilton Lane, is 1.3 miles from Ellis Landing Beach and 15 miles from Cape Cod Gateway Airport.
The 940-square-foot house features two bedrooms, two bathrooms, and accommodates up to nine guests, offering a private garden, swimming pool, jacuzzi, tennis court, and on-site restaurant and bar.
Lovely Home W/free Wifi/spacious Patio/spiral Staircase - Near Shops/restaurants - Chatham, MA
8.8 21 reviews

Lovely Home W/free Wifi/spacious Patio/spiral Staircase - Near Shops/restaurants

apartment, Brewster
This Brewster vacation rental, located 15 miles from Chatham, offers convenient access to Cape Cod Beaches, Cape Cod National Seashore, the Cape Cod Museum of Natural History, and Sheep Pond Woodlands Trail.
This 1070 sq ft, family-friendly apartment sleeps 6 and features a full kitchen, air conditioning, a swimming pool, jacuzzi, spa, and a private patio with a gas grill, with optional Ocean Edge pool/sports club passes available.
265 M² House ∙ 4 Bedrooms ∙ 11 Guests - Chatham, MA
9.8 10 reviews

265 M² House ∙ 4 Bedrooms ∙ 11 Guests

house, Harwich
Norma's Cape Escape, a spacious three-story house in Harwich, Massachusetts, is a short drive from Harwich Port beaches, Wequassett Resort (1.3 miles), and offers easy access to Dunkin', Starbucks, and Stop & Shop (1.7 miles).
This 2850-square-foot home sleeps 11, features 4 bedrooms, 3 bathrooms, a private spa, fitness center, and includes a $750 Xplorie package offering access to local attractions like Island Cruises and the Whydah Pirate Museum.

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.

Peaceful Retreat On Chilton Lane - Chatham, MA
10 1 review

Peaceful Retreat On Chilton Lane

apartment, Brewster
This Brewster apartment rental is conveniently located near Cape Cod beaches and attractions such as the Cape Cod Inflatable Park, offering easy access to other Cape Cod destinations.
This 940-square-foot condo boasts two bedrooms, two bathrooms, sleeps five, and includes amenities such as a fully equipped kitchen, free Wi-Fi, a balcony, an on-site water park, indoor pool, and hot tub.
Pool, Half Mile To Beach! - Chatham, MA
10 2 reviews

Pool, Half Mile To Beach!

apartment, Harwich
This Harwich vacation rental, located on a hilltop less than half a mile from Jackknife Beach and 0.4 miles from the Wequassett Resort, offers easy access to beaches, the Eastward Ho! Golf Course, and downtown Chatham.
This 2730-square-foot home features five bedrooms, four bathrooms, two living rooms, a game room, a private seasonal pool, and can comfortably accommodate ten guests, making it ideal for large families or groups seeking a Harwich getaway.
House ∙ 3 Bedrooms ∙ 8 Guests - Chatham, MA
9.6 5 reviews

House ∙ 3 Bedrooms ∙ 8 Guests

house, Chatham
Azure Cottage, located in Chatham's Oyster Pond area, is less than a mile from downtown Chatham and 1.2 miles from Oyster Pond.
This three-bedroom, two-bathroom Cape Cod-style home sleeps eight, boasts a private 3/4-acre lot with a pool, hot tub, and outdoor amenities, plus includes a $750 Xplorie package for local attractions.
Walk 2beach, Pool, Hot Tub, Gameroom, Petsok - Chatham, MA
10 13 reviews

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

apartment, Chatham
This four-bedroom apartment is located in Chatham, a short walk from Hardings Beach and a paddle board rental shop.
The 3,875 square foot home features a private pool and hot tub, a game room, a movie room, an outdoor kitchen, a fire pit, and a scenic walking trail, comfortably accommodating up to 10 guests.

Best Chatham, MA accommodation with a kitchen

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 vacation home is located in South Chatham, just a 15-minute walk from the Chatham Chamber of Commerce and Cape Cod Beaches. It has consistently received excellent ratings from previous guests for its cleanliness, location, and overall experience.
This spacious house offers 1,500 square feet of living space and can comfortably accommodate up to 10 guests. Enjoy a range of amenities, including a private swimming pool, a spa tub, a game room, and a garden with barbecue grills, perfect for relaxing and entertaining.
Waterfront Chatham Escape, Pet Friendly, Pond View - Chatham, MA
No reviews

Waterfront Chatham Escape, Pet Friendly, Pond View

apartment, Chatham
This pet-friendly waterfront apartment in Chatham offers direct access to Oyster Pond and is located in a quiet neighborhood, just minutes from Chatham's beaches, shops, and restaurants.
This 4-bedroom, 4-bathroom dwelling accommodates 10 guests and features a furnished patio with pond views, a BBQ grill, an outdoor shower, a pool table, and includes $750 in daily complimentary tickets to local attractions through its Xplorie partnership.
The Mansion At Ocean Edge Resort & Golf Club - Chatham, MA
8.3 2653 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.
Beautiful Chatham,  Sun Sand & Surf.  8/10 Mile To  Beaches ,Pet Friendly Home - Chatham, MA
10 44 reviews

Beautiful Chatham, Sun Sand & Surf. 8/10 Mile To Beaches ,Pet Friendly Home

apartment, Chatham
This South Chatham vacation rental is located in a peaceful cul-de-sac, a short walk from Cockle Cove Beach and a quick bike ride to Chatham's town center, offering easy access to Carmine's Cafe, ice cream shops, the Chatham Historical Society, and the Chatham Fish Pier.
This 1840-square-foot home features four bedrooms, three bathrooms, and accommodates eight guests, boasting a deck, microwave, dishwasher, air conditioning, internet, parking, and a garden.

Best Chatham, MA accommodation with a balcony

Beachside Harwich Port Apartment Near Town - Chatham, MA
No reviews

Beachside Harwich Port Apartment Near Town

apartment, Harwich
Chatham Bars Inn - Chatham, MA
9.2 1004 reviews

Chatham Bars Inn

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

Main Street Chatham Village Downtown-new Listing!

house, Chatham
Steps To Chatham's Historic Downtown - Chatham, MA
No reviews

Steps To Chatham's Historic Downtown

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.

Sand And Land! Tennis & Water Access! - Chatham, MA
9.9 100 reviews

Sand And Land! Tennis & Water Access!

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.

80 M² Cottage ∙ 1 Bedroom ∙ 4 Guests - Chatham, MA
9.6 21 reviews

80 M² Cottage ∙ 1 Bedroom ∙ 4 Guests

cottage, Chatham
The Perfect Beach Getaway! - Chatham, MA
9.2 53 reviews

The Perfect Beach Getaway!

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

Sarah-n-dipity: Cozy Cottage Near Ridgevale Beach

cottage, Chatham
Coastal Charm Space Galore At Norma's Escape - Chatham, MA
10 1 review

Coastal Charm Space Galore At Norma's Escape

house, Harwich

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.

Walk To Ridgevale Beach, Fabulous For Families - Chatham, MA
No reviews

Walk To Ridgevale Beach, Fabulous For Families

apartment, Chatham
©2026 cozycozy.com