First Encounter Beach Holiday Rentals

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

Charming Sun Filled Eastham Cottage at Fort Hill
10.0 (61 Reviews)
1 Bedroom 2 Guests
Sunroom Mins to Beaches Views of Marsh
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10.0 (4 Reviews)
4 Bedrooms 8 Guests
Whalewalk Inn and Spa
FromCA $413 per night
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10.0 (95 Reviews)
1 Bedroom 2 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
10.0 (51 Reviews)
2 Bedrooms 4 Guests
Seaside Retreat w Private Beach Landing
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10.0 (4 Reviews)
3 Bedrooms 6 Guests
The Parsonage Inn
FromCA $345 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
The Parsonage
FromCA $540 per night
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10.0 (4 Reviews)
10 Bedrooms 22 Guests
The Inn at the Oaks
FromCA $376 per night
9.2 (323 Reviews)
1 Bedroom 2 Guests
1 min drive to Rock Harbor, 2 min to Town!
10.0 (41 Reviews)
2 Bedrooms 5 Guests
4-5 Min to Mill Pond or Nauset Beach
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10.0 (2 Reviews)
4 Bedrooms 9 Guests
Great Waterfront Property, Kayak the National Park Seashore
10.0 (37 Reviews)
2 Bedrooms 6 Guests
Beach Getaway with Private Backyard
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10.0 (2 Reviews)
4 Bedrooms 10 Guests
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 (28 Reviews)
2 Bedrooms 4 Guests
Lovely House 5 Min to Beach with Deck Grill and Garage
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
The Breeze on Minister's Pond
10.0 (26 Reviews)
1 Bedroom 2 Guests
Dog Friend Waterfront Home
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 (25 Reviews)
2 Bedrooms 7 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
New Eastham Oceanside Guest Suite with Pool and Hot Tub
10.0 (24 Reviews)
1 Bedroom 2 Guests
Ocean Views New A C Dog Welcome
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10.0 (1 Review)
5 Bedrooms 11 Guests
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 (21 Reviews)
2 Bedrooms 5 Guests
Gorgeous Architectural Home w Water Views
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10.0 (1 Review)
4 Bedrooms 8 Guests
Cape Cod Sunscape. Orleans
FromCA $1,347 per night
10.0 (17 Reviews)
2 Bedrooms 6 Guests
Walk to Water Hot Tub & Game Room
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10.0 (1 Review)
5 Bedrooms 10 Guests
Cape Cod Cottage Retreat
FromCA $555 per night
10.0 (16 Reviews)
2 Bedrooms 4 Guests
Waterfront home with Hot Tub Firepit and Game Room
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10.0 (1 Review)
4 Bedrooms 8 Guests
3 Bicycles Provided! Cape Cod Cottage w/Deck
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10.0 (1 Review)
3 Bedrooms 6 Guests
Newly updated spacious steps to water
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10.0 (1 Review)
2 Bedrooms 4 Guests
3000 Sq Ft Home with Hot Tub
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10.0 (1 Review)
3 Bedrooms 8 Guests
Minutes to Private Association
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10.0 (1 Review)
4 Bedrooms 8 Guests
Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!
10.0 (11 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
Steps to Rock Harbor, Fully Renovated Cape Cod Cottage
10.0 (10 Reviews)
2 Bedrooms 6 Guests
Half Mile to Private Association Beach
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10.0 (1 Review)
2 Bedrooms 5 Guests
Edgewood on Campground Beach/Steps to the Sand
10.0 (9 Reviews)
2 Bedrooms 4 Guests
National Seashore/Updated/Game Room~Blue Pearl
10.0 (9 Reviews)
2 Bedrooms 6 Guests
Quiet Neighborhood .2 miles to Skaket Beach (1193)
10.0 (6 Reviews)
2 Bedrooms 6 Guests
Bed, Splash & Beyond – Coastal Comfort Awaits
10.0 (6 Reviews)
1 Bedroom 4 Guests
Family-friendly Oasis Steps from Kingsbury Beach
10.0 (3 Reviews)
2 Bedrooms 4 Guests
Refurbished Cottage with Views of Town Cove (1038)
10.0 (3 Reviews)
2 Bedrooms 4 Guests
Walk to Beach, Spacious Home and Private Backyard!
10.0 (2 Reviews)
2 Bedrooms 4 Guests
Vintage 1940s Cottage Near Beaches & Trails
10.0 (2 Reviews)
1 Bedroom 2 Guests
Cozy Cottage by Molls Pond 2409
10.0 (1 Review)
2 Bedrooms 4 Guests
Secluded Eastham Gem Near Beach & Bike Trail
10.0 (1 Review)
2 Bedrooms 5 Guests
Charming Waterfront Escape Along the Cove
10.0 (1 Review)
2 Bedrooms 4 Guests
Peaceful Covefront Cottage Retreat in Eastham
10.0 (1 Review)
2 Bedrooms 4 Guests
Tranquil Eastham Waterfront Cottage Escape
10.0 (1 Review)
2 Bedrooms 4 Guests
The Cherry, cozy, charming and romantic.
10.0 (1 Review)
1 Bedroom 2 Guests
Romantic Orleans Waterfront Cottage!
9.8 (31 Reviews)
1 Bedroom 2 Guests
🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 (25 Reviews)
2 Bedrooms 4 Guests
1940s Cottage Stunner Large Studio w/loft feel dog friendly
9.8 (23 Reviews)
1 Bedroom 3 Guests
Castaway Cottage on the bay~Dog Friendly Too!
9.8 (18 Reviews)
2 Bedrooms 5 Guests
Fantastic Orleans Waterfront 2BR Cottage
9.8 (17 Reviews)
2 Bedrooms 5 Guests
🐚The Bay Cottage on Thumpertown Beach
9.8 (13 Reviews)
2 Bedrooms 4 Guests
Cozy Cottage Overlooking Rock Harbor Creek
9.8 (10 Reviews)
1 Bedroom 4 Guests

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

Discover more than 969 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 1160.21 ft², with nightly prices averaging CA $859.

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 969 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 660
Pleasant Point Vacation Rentals in Eastham, Massachusetts 705
West Brewster Vacation Rentals in Eastham, Massachusetts 575
Sea Pines Vacation Rentals in Eastham, Massachusetts 731