Eastham Windmill Holiday Rentals

Compare Villas, Resorts, & Rentals in Eastham Windmill, Eastham, Massachusetts, USA

Driftwood Cottages - 85 - Lobster
New
3 Bedrooms 6 Guests
Seaside Retreat w Private Beach Landing
|
10.0 (4 Reviews)
3 Bedrooms 6 Guests
Whalewalk Inn and Spa
FromUS $239 per night
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10.0 (88 Reviews)
1 Bedroom 2 Guests
Walk to Water, Cozy, Dog Friendly!
New
3 Bedrooms 8 Guests
Sunroom Mins to Beaches Views of Marsh
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10.0 (3 Reviews)
4 Bedrooms 8 Guests
The Inn at the Oaks
FromUS $268 per night
9.2 (322 Reviews)
1 Bedroom 2 Guests
Game Room, Cozy & Mins to Beaches!
New
3 Bedrooms 6 Guests
4-5 Min to Mill Pond or Nauset Beach
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10.0 (2 Reviews)
4 Bedrooms 9 Guests
The Seagrove Suites & Guest Rooms
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9.2 (127 Reviews)
1 Bedroom 2 Guests
Truly Wonderful Cape Cottage
FromUS $272 per night
10.0 (134 Reviews)
1 Bedroom 2 Guests
Lovely House 5 Min to Beach with Deck Grill and Garage
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
Walk down quiet country lane to private Bay Beach.
10.0 (124 Reviews)
2 Bedrooms 5 Guests
Dog Friend Waterfront Home
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
Waterfront Cottage - Adorable & Private
10.0 (81 Reviews)
1 Bedroom 2 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
Ocean Views New A C Dog Welcome
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10.0 (1 Review)
5 Bedrooms 11 Guests
Charming Sun Filled Eastham Cottage at Fort Hill
10.0 (59 Reviews)
1 Bedroom 2 Guests
Gorgeous Architectural Home w Water Views
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10.0 (1 Review)
4 Bedrooms 8 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
10.0 (50 Reviews)
2 Bedrooms 4 Guests
Walk to Water Hot Tub & Game Room
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10.0 (1 Review)
5 Bedrooms 10 Guests
Waterfront home with Hot Tub Firepit and Game Room
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10.0 (1 Review)
4 Bedrooms 8 Guests
1 min drive to Rock Harbor, 2 min to Town!
10.0 (39 Reviews)
2 Bedrooms 5 Guests
3000 Sq Ft Home with Hot Tub
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10.0 (1 Review)
3 Bedrooms 8 Guests
Great Waterfront Property, Kayak the National Park Seashore
10.0 (36 Reviews)
2 Bedrooms 6 Guests
Short Walk to Private Association Beach
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10.0 (1 Review)
3 Bedrooms 6 Guests
Walk to Coast Guard Beach! Peaceful Vacation
10.0 (36 Reviews)
2 Bedrooms 3 Guests
Stunning Bay Views by Beach Dog Friendly
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10.0 (1 Review)
3 Bedrooms 7 Guests
Cottage over looking Coast Guard Beach and the Atlantic
10.0 (36 Reviews)
1 Bedroom 2 Guests
Newly updated spacious steps to water
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10.0 (1 Review)
2 Bedrooms 4 Guests
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 (27 Reviews)
2 Bedrooms 4 Guests
2 Miles to Nauset & Coast Guard Beach Dog Friendly
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10.0 (1 Review)
6 Bedrooms 12 Guests
The Breeze on Minister's Pond
10.0 (25 Reviews)
1 Bedroom 2 Guests
Half Mile to Private Association Beach
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10.0 (1 Review)
2 Bedrooms 5 Guests
The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 (23 Reviews)
2 Bedrooms 7 Guests
Beach & Golf Hub w/All-Season Sunroom in Cape Cod
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10.0 (1 Review)
5 Bedrooms 9 Guests
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 (19 Reviews)
2 Bedrooms 5 Guests
The Tranquil Heron Cottage
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9.8 (5 Reviews)
1 Bedroom 6 Guests
Cape Cod Sunscape. Orleans
10.0 (17 Reviews)
2 Bedrooms 6 Guests
New Eastham Oceanside Guest Suite with Pool and Hot Tub
10.0 (16 Reviews)
1 Bedroom 2 Guests
Cape Cod Cottage Retreat
FromUS $351 per night
10.0 (15 Reviews)
2 Bedrooms 4 Guests
National Seashore/Updated/Game Room~Blue Pearl
10.0 (9 Reviews)
2 Bedrooms 6 Guests
Adorable home in the heart of East Orleans!
9.8 (28 Reviews)
2 Bedrooms 5 Guests
Beautiful Spacious Family Retreat w Pool
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
Eagle Wing Inn - Cape Cod
FromUS $134 per night
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9.8 (425 Reviews)
1 Bedroom 2 Guests
🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 (24 Reviews)
1 Bedroom 4 Guests
4 Bedroom Home by Leavetown Vacations
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
Endless Dunes, A Modern Motel
9.0 (139 Reviews)
1 Bedroom 2 Guests
1940s Cottage Stunner Large Studio w/loft feel dog friendly
9.8 (22 Reviews)
1 Bedroom 3 Guests
Inn at the Oaks
FromUS $390 per night
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9.6 (34 Reviews)
13 Bedrooms 31 Guests
Viking Shores Motor Inn
FromUS $93 per night
8.6 (125 Reviews)
1 Bedroom 2 Guests
Fantastic Orleans Waterfront 2BR Cottage
9.8 (17 Reviews)
2 Bedrooms 5 Guests
Bike to Nauset Beach or Walk to Mill Pond
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9.5 (11 Reviews)
3 Bedrooms 6 Guests
Castaway Cottage on the bay~Dog Friendly Too!
9.8 (13 Reviews)
2 Bedrooms 5 Guests
Minutes to Oceanside Beaches
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9.5 (10 Reviews)
3 Bedrooms 6 Guests
🐚The Bay Cottage on Thumpertown Beach
9.8 (11 Reviews)
2 Bedrooms 4 Guests
Dreamy Cottage for Two Close to Beaches
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9.5 (2 Reviews)
1 Bedroom 2 Guests
Cozy Cottage Overlooking Rock Harbor Creek
9.8 (10 Reviews)
1 Bedroom 4 Guests
Four Season Modern Cape Cod Cottage (with heat)
9.4 (6 Reviews)
2 Bedrooms 4 Guests
Newly Renovated Cottage on Town Cove!
9.8 (9 Reviews)
2 Bedrooms 4 Guests
Perfect Relaxation Spot 5 min to Beach
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9.4 (5 Reviews)
3 Bedrooms 8 Guests
Waterfront amazing views near beaches
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9.3 (3 Reviews)
3 Bedrooms 6 Guests
Private Road - Near Bike Trail & Beaches
9.6 (35 Reviews)
2 Bedrooms 4 Guests
Great Home with Game Space 0 8 miles from Cooks Brook Beach
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9.0 (2 Reviews)
4 Bedrooms 8 Guests
Great Location Near Cape Cod National Seashore
9.6 (33 Reviews)
2 Bedrooms 4 Guests
Gray Gables
FromUS $670 per night
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9.0 (2 Reviews)
1 Bedroom 6 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
9.6 (29 Reviews)
2 Bedrooms 4 Guests
Pine Grove Cottage
FromUS $120 per night
|
9.0 (2 Reviews)
2 Bedrooms 2 Guests

About Casai's Private Villas and Holiday Rentals in Eastham Windmill

Discover more than 978 vacation rentals available in Eastham Windmill. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Eastham Windmill.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Eastham Windmill, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Eastham Windmill. On average, places to stay near Eastham Windmill offer 1101.73 ft², with nightly prices averaging US $601.

With Casai, finding and comparing holiday rentals in Eastham Windmill is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Frequently Asked Questions About Eastham Windmill?

What are the top holiday rentals in Eastham Windmill?

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As of 2026, Casai boasts over 978 properties listed in the Eastham Windmill area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Eastham Windmill.

Nearby Neighborhood (4)

NeighborhoodProperty Count
Indian Neck Heights Vacation Rentals in Eastham, Massachusetts 24
Pleasant Point Vacation Rentals in Eastham, Massachusetts 672
West Brewster Vacation Rentals in Eastham, Massachusetts 574
Sea Pines Vacation Rentals in Eastham, Massachusetts 725