A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Family friendly Hotels in Chatham, Massachusetts

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Check availability on Chatham Family friendly Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chatham family-friendly hotels

A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A restaurant with long communal tables and booths, large windows, and a view of buildings outside.
An outdoor seating area with tables and chairs, a sign for 'Wild Goose Tavern', and large windows.
A garden with a pergola structure, a pathway, and a seating area.

1. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
  • Beach vacation bliss for kids and adults with complimentary bicycles, pool loungers, and family-friendly outdoor activities.
P11,222
P15,569 total
includes taxes & fees
Oct 29 - Oct 30
Chatham Wayside Inn
A swimming pool with lounge chairs and a poolside area.
A modern bathroom with a double sink vanity, a large mirror, and a glass-enclosed shower area.
A white house with a grey roof, surrounded by a well-maintained lawn and flowering bushes.
A modern kitchen with white cabinetry, a wooden island with two barstools, and a decorative wall art piece.

2. Greyfinch Chatham Inn

Greyfinch Chatham Inn
Chatham
  • Family-friendly Cape Cod retreat offers renovated rooms, seasonal pool, and complimentary bicycles just minutes from the beach.
P10,066
P13,815 total
includes taxes & fees
Nov 1 - Nov 2
Greyfinch Chatham Inn
A beach with people sunbathing and swimming, a rocky shoreline, and houses in the background.
A modern bathroom with a glass shower enclosure, a white sink with a mirror above, and two rolls of toilet paper on the left.
A covered porch with wicker furniture and a red cushion, a brick pathway, and a grassy area with a sign in the background.
A dining area with a round table and white chairs, a staircase, and a blue accent wall.

3. Surfside Inn Chatham

Surfside Inn Chatham
Chatham
P14,707
P16,832 total
includes taxes & fees
Oct 4 - Oct 5
Surfside Inn Chatham
A water play area with a ship-themed slide and a fountain.
A balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.
A pool area with lounge chairs and a fire pit, surrounded by stone walls and potted plants.
A dining area with tables set for two, overlooking a body of water with a sailboat.

4. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • Resort paradise with seasonal outdoor pool, kids' club, and playground makes family memories on a private beach.
P25,327
P31,016 total
includes taxes & fees
Oct 19 - Oct 20
Wequassett Resort and Golf Club
A room with a bed, two wicker chairs, a small table, a coffee maker, and a view of the sea through a window.
A deck with a view of the ocean, a blue umbrella, and a white chair.
A coastal house with a deck, outdoor seating, and a view of the sea.
A view from a window with white frames, overlooking a beach area with a house, a blue chair, and a wooden deck.

5. Chatham Tides

Chatham Tides
South Chatham
P14,025
P16,051 total
includes taxes & fees
Oct 28 - Oct 29
Chatham Tides
A hotel room with a large bed, teal walls, and a wooden headboard. There are two bedside tables with lamps and small plants.
A kitchen with a brick stove, a white countertop, and a sign labeled "POOL TOWELS".
A dining area with round tables and chairs, floral centerpieces, and decorative wall signs.
A traditional fireplace with a clock above it, surrounded by various decorative items and a modern refrigerator.

6. Olde Tavern Motel And Inn

Olde Tavern Motel And Inn
Orleans
P6,196
P7,091 total
includes taxes & fees
Oct 4 - Oct 5
Olde Tavern Motel And Inn
A balcony with a view of a beach, a table with a vase of flowers, and a chair.
A room with large windows overlooking a beach, a table with a bottle and glasses, and a chair.
A spacious living room with a large window, a ceiling fan, and a glass coffee table with flowers.
A beachfront property with a patio area, outdoor seating, and a view of the ocean.

7. Winstead Beach Resort

Winstead Beach Resort
Harwich Port
P14,008
P16,032 total
includes taxes & fees
Oct 5 - Oct 6
Winstead Beach Resort
A beach with clear water, a sandy shore, and houses in the background.
A modern bathroom with a glass shower enclosure, a white sink, and a towel rack.
A staircase with wooden steps and a white wall. There is a white sofa with a geometric pillow in the living area.
A cozy living room with a fireplace, striped sofa, wooden flooring, and exposed beams.

8. Kingfisher Harwich Port

Kingfisher Harwich Port
Harwich Port
P14,371
P16,447 total
includes taxes & fees
Oct 4 - Oct 5
Kingfisher Harwich Port
A garden area with a welcome sign, outdoor seating, and a blue umbrella.
A hotel reception area with a blue wall, a reception desk, a large window, and a welcome mat.
A hotel room with a large bed, two bedside tables, a wall-mounted painting, and a patterned carpet.
A bathroom with a shower curtain, a bathtub, and a tiled wall with a marble-like pattern.

9. Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod
Orleans
P6,539
P7,484 total
includes taxes & fees
Oct 4 - Oct 5
Rodeway Inn Orleans - Cape Cod
A two-story house with a front porch, a mailbox, and a well-maintained garden.
A covered porch with white Adirondack chairs, a trash can, and a door marked with the number 9.
A modern interior with a wooden floor, a blue and white patterned wall, a large painting, and a bar area with a blue marble backsplash.
A swimming pool with lounge chairs and a covered seating area.

10. Pelham on Earle

Pelham on Earle
West Harwich
P11,828
P14,620 total
includes taxes & fees
Oct 30 - Oct 31
Pelham on Earle
View all properties

Choose what matters most at family-friendly hotels in Chatham

Pool
Breakfast included
4 stars
All-inclusive
5 stars

Top Chatham Hotel Reviews

Riviera Beach Resort

Riviera Beach Resort

10/10 Excellent
"Clean, pool was great and heated !"
Melanie 4-night trip
Posted 3 hours ago
Riviera Beach Resort
Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"Nice hotel, restaurant with nice outdoor setting."
Monique 1-night trip
Posted 5 hours ago
Uncommoner Hotel by Reverie Boutique Collection
Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Clean rooms and very helpful staff."
Louie 1-night trip
Posted 1 day ago
Hyannis Travel Inn
Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Staff was excellent hotel clean"
Jerome 2-night trip
Posted 1 day ago
Cape Sands Inn
Pleasant Bay Village Resort

Pleasant Bay Village Resort

10/10 Excellent
"Everything was exceptional!"
sheila 1-night trip
Posted 5 days ago
Pleasant Bay Village Resort
Greyfinch Chatham Inn

Greyfinch Chatham Inn

10/10 Excellent
"This place is so cute! When we first pulled up we were unsure because it looks like an old roadside motel. But it’s quickly apparent that it’s been beautifully updated with fresh paint and hanging plants. The driveway and parking lot are spotless as are the rooms. The decor in the rooms is updated and coastal. The staff was lovely. I would absolutely stay here again!"
Robert 4-night trip
Posted 7 days ago
Greyfinch Chatham Inn

Frequently asked questions

What's Chatham like for family-friendly vacations?
The destination of Chatham is a great choice if you've been thinking about a vacation with your kids. The beaches, baseball games, and seafood restaurants are just some of the things that make this an attractive family vacation spot. Arrange a flight into Hyannis, MA (HYA-Barnstable Municipal), which is located 16.8 mi (27 km) from the city center.
What's the best place to stay for a family vacation to Chatham?
Chatham Wayside Inn is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families. Greyfinch Chatham Inn is another good choice for your kid-friendly vacation.
When's the best time to book a family-friendly vacation in Chatham?
The hottest months are usually August and July with an average temp of 67°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Chatham is 54 inches.
What's there to see and do with your family in Chatham?
While you are visiting Chatham, you and the family might want to check out some interesting spots such as Veterans Field, Chase Park, and Chatham Drama Guild. Make sure you have lots of time for activities like Atwood House Museum and Gallery Antonia.

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