First Encounter Beach Holiday Rentals

Compare Villas, Resorts, & Rentals in First Encounter Beach, Eastham, Massachusetts, USA

Walk to Water, Cozy, Dog Friendly!
New
3 Bedrooms 8 Guests
Seaside Retreat w Private Beach Landing
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10.0 (3 Reviews)
3 Bedrooms 6 Guests
The Parsonage Inn
FromCA $342 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
Game Room, Cozy & Mins to Beaches!
New
3 Bedrooms 6 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
FromCA $372 per night
9.2 (322 Reviews)
1 Bedroom 2 Guests
Truly Wonderful Cape Cottage
FromCA $358 per night
10.0 (134 Reviews)
1 Bedroom 2 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
Walk down quiet country lane to private Bay Beach.
10.0 (124 Reviews)
2 Bedrooms 5 Guests
Lovely House 5 Min to Beach with Deck Grill and Garage
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
Waterfront Cottage - Adorable & Private
10.0 (81 Reviews)
1 Bedroom 2 Guests
Dog Friend Waterfront Home
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
Charming Sun Filled Eastham Cottage at Fort Hill
10.0 (59 Reviews)
1 Bedroom 2 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
10.0 (50 Reviews)
2 Bedrooms 4 Guests
Ocean Views New A C Dog Welcome
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10.0 (1 Review)
5 Bedrooms 11 Guests
Gorgeous Architectural Home w Water Views
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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
Walk to Water Hot Tub & Game Room
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10.0 (1 Review)
5 Bedrooms 10 Guests
Great Waterfront Property, Kayak the National Park Seashore
10.0 (36 Reviews)
2 Bedrooms 6 Guests
Waterfront home with Hot Tub Firepit and Game Room
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10.0 (1 Review)
4 Bedrooms 8 Guests
Beach Getaway with Private Backyard
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10.0 (1 Review)
4 Bedrooms 10 Guests
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 (27 Reviews)
2 Bedrooms 4 Guests
3000 Sq Ft Home with Hot Tub
FromCA $1,388 per night
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10.0 (1 Review)
3 Bedrooms 8 Guests
The Breeze on Minister's Pond
10.0 (25 Reviews)
1 Bedroom 2 Guests
Newly updated spacious steps to water
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10.0 (1 Review)
2 Bedrooms 4 Guests
The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 (23 Reviews)
2 Bedrooms 7 Guests
2 Miles to Nauset & Coast Guard Beach Dog Friendly
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10.0 (1 Review)
6 Bedrooms 12 Guests
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 (19 Reviews)
2 Bedrooms 6 Guests
Half Mile to Private Association Beach
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10.0 (1 Review)
2 Bedrooms 5 Guests
Cape Cod Sunscape. Orleans
10.0 (17 Reviews)
2 Bedrooms 6 Guests
Beach and Golf Hub with All-Season Sunroom in Cape Cod
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10.0 (1 Review)
5 Bedrooms 9 Guests
The Parsonage
FromCA $535 per night
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9.8 (9 Reviews)
10 Bedrooms 22 Guests
Cape Cod Cottage Retreat
FromCA $494 per night
10.0 (15 Reviews)
2 Bedrooms 4 Guests
The Tranquil Heron Cottage
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9.8 (5 Reviews)
1 Bedroom 6 Guests
New Eastham Oceanside Guest Suite with Pool and Hot Tub
10.0 (15 Reviews)
1 Bedroom 2 Guests
Steps to private bay beach 0.2 mi. Central AC.
10.0 (13 Reviews)
2 Bedrooms 8 Guests
Steps to Rock Harbor, Fully Renovated Cape Cod Cottage
10.0 (9 Reviews)
2 Bedrooms 6 Guests
1940s Cottage Stunner Large Studio w/loft feel dog friendly
9.8 (22 Reviews)
1 Bedroom 3 Guests
Beautiful Spacious Family Retreat w Pool
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
Eagle Wing Inn - Cape Cod
FromCA $183 per night
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9.8 (425 Reviews)
1 Bedroom 2 Guests
Fantastic Orleans Waterfront 2BR Cottage
9.8 (17 Reviews)
2 Bedrooms 5 Guests
4 Bedroom Home by Leavetown Vacations
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
Olde Tavern Motel And Inn
FromCA $348 per night
9.4 (237 Reviews)
1 Bedroom 2 Guests
Castaway Cottage on the bay~Dog Friendly Too!
9.8 (13 Reviews)
2 Bedrooms 5 Guests
Inn at the Oaks
FromCA $542 per night
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9.6 (34 Reviews)
13 Bedrooms 31 Guests
Skaket Beach Motel
FromCA $159 per night
9.2 (450 Reviews)
1 Bedroom 2 Guests
🐚The Bay Cottage on Thumpertown Beach
9.8 (11 Reviews)
2 Bedrooms 4 Guests
Bike to Nauset Beach or Walk to Mill Pond
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9.5 (11 Reviews)
3 Bedrooms 6 Guests
Cozy Cottage Overlooking Rock Harbor Creek
9.8 (10 Reviews)
1 Bedroom 4 Guests
Newly Renovated Cottage on Town Cove!
9.8 (9 Reviews)
2 Bedrooms 4 Guests
Minutes to Oceanside Beaches
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9.4 (9 Reviews)
3 Bedrooms 6 Guests
Perfect Relaxation Spot 5 min to Beach
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9.4 (5 Reviews)
3 Bedrooms 8 Guests
Private Road - Near Bike Trail & Beaches
9.6 (35 Reviews)
2 Bedrooms 4 Guests
Waterfront amazing views near beaches
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9.3 (3 Reviews)
3 Bedrooms 6 Guests
Great Location Near Cape Cod National Seashore
9.6 (33 Reviews)
2 Bedrooms 4 Guests
Steps to Skaket Beach
FromCA $1,254 per night
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9.0 (3 Reviews)
4 Bedrooms 8 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
9.6 (29 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
Beachfront on Cape Cod Bay in Eastham! (1039)
9.6 (24 Reviews)
2 Bedrooms 6 Guests
Gray Gables
FromCA $931 per night
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9.0 (2 Reviews)
1 Bedroom 6 Guests
Clean and Quiet North Eastham Cottage Near Beaches
9.6 (20 Reviews)
3 Bedrooms 6 Guests
Pine Grove Cottage
FromCA $167 per night
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9.0 (2 Reviews)
2 Bedrooms 2 Guests

About Casai's Private Villas and Holiday Rentals in First Encounter Beach

Discover more than 945 vacation rentals available in First Encounter Beach. 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 First Encounter Beach.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in First Encounter Beach, 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 First Encounter Beach. On average, places to stay near First Encounter Beach offer 1099.62 ft², with nightly prices averaging CA $852.

With Casai, finding and comparing holiday rentals in First Encounter Beach 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 First Encounter Beach?

What are the top holiday rentals in First Encounter Beach?

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As of 2026, Casai boasts over 945 properties listed in the First Encounter Beach area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in First Encounter Beach.

Nearby Neighborhood (4)

NeighborhoodProperty Count
Indian Neck Heights Vacation Rentals in Eastham, Massachusetts 25
Pleasant Point Vacation Rentals in Eastham, Massachusetts 673
West Brewster Vacation Rentals in Eastham, Massachusetts 544
Sea Pines Vacation Rentals in Eastham, Massachusetts 701