Eastham Vacation Homes

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

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Our top choices for Eastham holiday homes

An outdoor deck with a grill, dining table, chairs, and an umbrella.

1. Sleeps 2-8/Soaking Tub/FirePit~Burrows

Eastham

Lourdes P.

HK$4,091 total

includes taxes & fees

1 Nov - 2 Nov

A living room with a grey sofa, striped rug, and a lamp.

2. The Pet-Friendly Surf Shack Hideaway on the Cove

Eastham

"We had such a wonderful time at the Surf Shack. The location was perfect. Within 15 minutes the best beaches, best dining, best shopping..everything. The house was incredibly clean with all the amenities needed to have a great family vacation. The host was incredibly quick to reply to any and all inquiries and was so pleasant to deal with. We couldn’t be any happier with our stay and will definitely stay there again if our travels return us to the Cape."

Justin R.

HK$3,973 total

includes taxes & fees

28 Oct - 29 Oct

A sliding glass door leading to an outdoor patio with a view of a lake, red and beige outdoor furniture, and a fire pit.

3. Pond House~Waterfront Oasis on Minister's Pond

Eastham

BILL

HK$4,101 total

includes taxes & fees

19 Oct - 20 Oct

A dining table set with plates, glasses, and a variety of food including grapes, cheese, and crackers.

4. National Seashore/Updated/Game Room~Blue Pearl

Eastham

Catharine D.

HK$3,954 total

includes taxes & fees

22 Oct - 23 Oct

Living room with plenty of seating and beautiful coastal design

5. Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Eastham

Donna R.

HK$5,197 total

includes taxes & fees

26 Oct - 27 Oct

A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

6. Lovely House 5 Min to Beach with Deck, Grill, Garage

Eastham

Susan C.

HK$3,581 total

includes taxes & fees

18 Oct - 19 Oct

A patio with Adirondack chairs, a fire pit, and a wooden deck.

7. Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Eastham

Susan W.

HK$3,295 total

includes taxes & fees

19 Oct - 20 Oct

A wooden outdoor shed with a door, a window, and a gravel path leading to it.

8. Gray Whale-Minutes to Eastham Bay & Ocean Beaches

Eastham

Leonard

HK$4,454 total

includes taxes & fees

18 Oct - 19 Oct

A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

9. Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Eastham

mark A.

HK$4,055 total

includes taxes & fees

18 Oct - 19 Oct

A beach with a wooden fence and a clear view of the ocean.

10. The Alpine/Walk to Beach for 2 or more!

Eastham

Jennifer G.

HK$4,094 total

includes taxes & fees

18 Oct - 19 Oct

A sandy beach with wooden posts and a clear view of the ocean.

11. Sand Bar~3 BR Dog Friendly Beachside Home

Eastham

Debra H.

HK$4,049 total

includes taxes & fees

26 Oct - 27 Oct

A wooden table set outdoors with plates, glasses, a bottle, and a metal container.

12. Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Eastham

David

HK$4,402 total

includes taxes & fees

28 Oct - 29 Oct

A table set for two with a view of the sunset over the water, outdoor seating, and a grill area.

13. Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

Eastham

Tereasa F.

HK$4,372 total

includes taxes & fees

28 Oct - 29 Oct

A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

14. 10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

HK$4,190 total

includes taxes & fees

27 Oct - 28 Oct

A deck with outdoor seating and a view of the ocean at sunset.

15. Beachfront~Seaside Sea-duction-Dog Friendly

Eastham

Keith B.

A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

16. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

Eastham

Mark T R.

HK$7,979 total

includes taxes & fees

28 Oct - 29 Oct

A beach with waves lapping onto the shore, a clear sky, and a sandy landscape.

17. Lovely Dog Friendly Beach Home Close to Everything. 5 and 6 day stay open July

Eastham

Jeanne B.

HK$4,086 total

includes taxes & fees

24 Oct - 25 Oct

A wooden deck with a table and chairs, an umbrella, and a view of the sea.

18. Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet

edyta d.

HK$3,997 total

includes taxes & fees

15 Nov - 16 Nov

A dining area with a wooden table set for four, surrounded by chairs. A large mirror hangs on the wall, reflecting the room.

19. Ebb Tide~3b/2b and dog friendly for 2-10

Wellfleet

Ross M.

HK$4,415 total

includes taxes & fees

19 Oct - 20 Oct

A cozy cabin interior with a wooden interior, a dining area, a sofa, and a staircase.

20. New! Island Pines-A Dog Friendly Boutique Oasis

Wellfleet

Kaden P.

HK$4,367 total

includes taxes & fees

4 Nov - 5 Nov

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Top Eastham Hotel Reviews

Ocean Park Inn

10/10 Excellent

"Clean & quiet, I felt safe as a solo female traveler."

Lovely Dog Friendly Beach Home Close to Everything. 5 and 6 day stay open July

10/10 Excellent

"This was a great base for our family of 5 over Columbus Day weekend, well stocked and close to many outer Cape attractions. The house is more spacious than it might appear from the road and gave us plenty of room to spread out. TV and wifi performed without a hitch. A grocery store and liquor store are less than 5 miles away in Orleans. For dinner out, we highly recommend Casa del Cabo just down the road, especially for seafood fans."

🐚The Bay Cottage on Thumpertown Beach

10/10 Excellent

"We enjoyed our stay here. It was very clean and well equipped. The kitchen was efficient. Communication with the host was very good. I also found the location to be perfect for us to explore beaches, see seals and travel to Provincetown as well as Chatham and Orleans. We would love to go back."

Castaway Cottage on the bay~Dog Friendly Too!

8/10 Good

"The cottage is smaller than expected, even for a cottage, but it was exceptionally clean and had everything we needed. The beach is only steps away and there is a great view of the bay from the yard. We enjoyed the property and surrounding areas. Sunsets were stunning!!"

New Eastham Oceanside Guest Suite with Pool and Hot Tub

10/10 Excellent

"We absolutely loved our stay. The place was cute, spotless and had quality furnishings. The bed was very comfortable, and we had a great set up for coffee in the morning. The yard is very pretty and we really enjoyed sitting on the deck. And the hosts were so nice and helpful-we got an early check-in and they responded immediately to our questions. We rent on the cape pretty often and this place was one of the best."

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