A house with a tower silhouetted against a vibrant sunset sky.

Luxury Hotels in Eastham, Massachusetts

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Eastham Luxury Hotels

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Eastham luxury hotels

A large, red-roofed building with a stone facade, surrounded by well-maintained gardens and a cobblestone driveway.
A beach with numerous blue umbrellas and lounge chairs.
An outdoor patio with tables and chairs, umbrellas, and a bar area.
An outdoor bar area with multiple screens displaying sports, surrounded by patrons.

1. The Mansion at Ocean Edge

The Mansion at Ocean Edge
Brewster
  • Coastal luxury flourishes at this historic Brewster hotel with a private beach, 5 spa treatment rooms, and championship golf.
P10,776
P15,924 total
includes taxes & fees
Oct 25 - Oct 26
The Mansion at Ocean Edge
A two-story house with a symmetrical facade, a central entrance, and a flag.
A living room with two armchairs, a sofa, a fireplace, and a window with curtains.
A neatly made bed with white bedding, two bedside tables with lamps, and a book on the bed.
A table set outdoors with a glass of iced tea, a glass of lemonade, and a bowl of fruit salad.

2. Candleberry Inn on Cape Cod

Candleberry Inn on Cape Cod
Brewster
  • Coastal luxury retreat near Breakwater Beach offers pampering spa services and Italian linens in a serene Cape Cod setting.
P16,940
P19,389 total
includes taxes & fees
Oct 27 - Oct 28
Candleberry Inn on Cape Cod
A balcony with wicker furniture, a table with a vase and wine glass, and a view of the sea.
A sunlit room with a view of the sea, featuring a sofa, a round table, and a chair.
A room with a view of the sea, featuring a sofa, two chairs, a small table with a vase and a bottle, and a patterned carpet.
A dining area with tables set for two, overlooking a body of water with a sailboat.

3. Wequassett Resort and Golf Club

Wequassett Resort and Golf Club
Harwich
  • Seaside luxury awaits on a private beach with 6 restaurants and ocean-view dining.
P25,392
P31,095 total
includes taxes & fees
Oct 19 - Oct 20
Wequassett Resort and Golf Club
A two-story house with a porch, a star decoration, and outdoor seating.
A dining table with a plate of food, a mug, and a bowl of berries.
A house with a blue door and a number '187' on the front.
A spacious living room with large windows, a patterned rug, and two sofas.

4. Sea Meadow Inn

Sea Meadow Inn
Brewster
P15,656
P18,187 total
includes taxes & fees
Oct 1 - Oct 2
Sea Meadow Inn
A sandy beach path with a wooden fence leading to the ocean, under a partly cloudy sky.
A garden with a pergola structure, a pathway, and a seating area.
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.

5. Chatham Wayside Inn

Chatham Wayside Inn
Chatham
P22,531
P28,516 total
includes taxes & fees
Oct 11 - Oct 12
Chatham Wayside Inn
A pathway leading to a beach with boats in the background and a building with a tower.
A deck with white Adirondack chairs and a small round table, overlooking a beach and ocean.
An aerial view of a beach with rows of sunbeds and umbrellas, a pier extending into the water, and a small building near the beach.
A hotel entrance with a sign reading "Chatham Bars Inn Cape Cod".

6. Chatham Bars Inn

Chatham Bars Inn
Chatham
  • Indulge in seaside luxury at this 5-star Chatham resort offering a private beach, full-service spa, and exceptional concierge service.
P25,066
P28,688 total
includes taxes & fees
Oct 20 - Oct 21
Chatham Bars 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 two-story building with a sign reading "Winston Inn and Boardwalk."
A spacious living room with a large window, a ceiling fan, and a glass coffee table with flowers.

7. Winstead Beach Resort

Winstead Beach Resort
Harwich Port
P12,056
P13,798 total
includes taxes & fees
Sep 28 - Sep 29
Winstead Beach Resort
A beach with a sunset, calm water, and rocks.
A covered outdoor seating area with wicker furniture and a blue cushioned sofa.
A bar area with a wooden barrel, glasses, candles, and a martini glass.
A dining area with wicker furniture, wooden tables, and large windows with views of trees.

8. The Old Manse Inn

The Old Manse Inn
Brewster
  • Charming Cape Cod getaway offers champagne service, garden retreats, and a delicious breakfast just steps from the beach.
P22,362
P25,592 total
includes taxes & fees
Oct 1 - Oct 2
The Old Manse Inn
A two-story house with a well-lit front porch, a staircase leading to the entrance, and a garden with various plants and flowers.
A corner building with a curved roof, large windows, and a well-maintained garden with various plants and flowers.
A large swimming pool with a fountain, surrounded by lounge chairs and umbrellas, set against a stone building with multiple windows and a balcony.
A cozy living room with a fireplace, a Christmas tree, and festive decorations.

9. Winstead Inn

Winstead Inn
Harwich
  • Harwich beach guesthouse provides luxury accommodations near sand, featuring heated pool amid gardens.
P16,470
P18,850 total
includes taxes & fees
Sep 28 - Sep 29
Winstead Inn
A table set with plates, glasses, a mug, and a blue hydrangea.
A swimming pool with a fountain, surrounded by greenery and a gazebo.
A garden with a white pergola, various plants, and a large tree.
A two-story building with a sign reading "The Orchard House."

10. Brewster by the Sea Inn

Brewster by the Sea Inn
West Brewster
Brewster by the Sea Inn
View all properties

Top Eastham Hotel Reviews

Eagle Wing Inn - Cape Cod

Eagle Wing Inn - Cape Cod

10/10 Excellent
"Lovely clean place . Nice continental breakfast . And who knew about the backyard deck! The bathroom was spotless but really small is my only critique."
Walter 1-night trip
Posted 12 hours ago
Eagle Wing Inn - Cape Cod

Frequently asked questions

Are you looking for a luxury hotel for your stay in Eastham?
Expedia can help you get a flight to Hyannis, MA (HYA-Barnstable Municipal) airport or Provincetown, MA (PVC-Provincetown Municipal) airport, and then you can select from a variety of places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a trip, so we make it easy to get what you need to make your stay relaxing and comfortable. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can help you find the best luxury hotel experience that Eastham offers. During your visit, you might want to enjoy the biking and hiking which Eastham is known for.
When can I expect good weather in Eastham?
Planning for the weather is an important factor for making your trip to Eastham a success, especially when you're splurging. The hottest months are usually August and July with an average temp of 66°F, while the coldest months are February and January with an average of 38°F. Average annual precipitation for Eastham is 53 inches.
What's there to see and do in Eastham?
Take in some sights and attractions while you're in Eastham by visiting Nauset Light Beach, Nauset Beach, and First Encounter Beach. If you have spare time during your trip, you might want to make a stop at Nauset Lighthouse and Cape Cod National Seashore.

Explore a world of travel with Expedia