First Encounter Beach Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in First Encounter Beach, Eastham, Massachusetts, USA

Sunroom Mins to Beaches Views of Marsh
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10.0 (3 Reviews)
4 Bedrooms 8 Guests
The Parsonage Inn
FromGB £183 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
New Game Room, Firepit, Mins to Beaches!
New
4 Bedrooms 8 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
Seaside Retreat w Private Beach Landing
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10.0 (2 Reviews)
3 Bedrooms 6 Guests
Eagle Wing Inn - Cape Cod
FromGB £98 per night
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9.8 (425 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
Truly Wonderful Cape Cottage
FromGB £182 per night
10.0 (134 Reviews)
1 Bedroom 2 Guests
Dog Friend Waterfront Home
FromGB £439 per night
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
Walk down quiet country lane to private Bay Beach.
10.0 (124 Reviews)
2 Bedrooms 5 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
Waterfront Cottage - Adorable & Private
10.0 (81 Reviews)
1 Bedroom 2 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, All New Interior
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
Beach Getaway with Private Backyard
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10.0 (1 Review)
4 Bedrooms 10 Guests
Great Waterfront Property, Kayak the National Park Seashore
10.0 (36 Reviews)
2 Bedrooms 6 Guests
3000 Sq Ft Home with Hot Tub
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10.0 (1 Review)
3 Bedrooms 8 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
FromGB £205 per night
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 (22 Reviews)
2 Bedrooms 7 Guests
Beach and Golf Hub with 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 (18 Reviews)
2 Bedrooms 6 Guests
The Parsonage
FromGB £1,566 per night
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9.8 (9 Reviews)
10 Bedrooms 22 Guests
Cape Cod Sunscape. Orleans
FromGB £485 per night
10.0 (17 Reviews)
2 Bedrooms 6 Guests
The Tranquil Heron Cottage
FromGB £308 per night
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9.8 (5 Reviews)
3 Bedrooms 6 Guests
Cape Cod Cottage Retreat
FromGB £262 per night
10.0 (15 Reviews)
2 Bedrooms 4 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
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
Olde Tavern Motel And Inn
FromGB £186 per night
9.4 (237 Reviews)
1 Bedroom 2 Guests
🦀Waterfront at The Velvet Crab~Amazing Sunsets
9.8 (23 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
Bike to Nauset Beach or Walk to Mill Pond
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9.5 (11 Reviews)
3 Bedrooms 6 Guests
Four Points by Sheraton Eastham Cape Cod
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8.2 (878 Reviews)
1 Bedroom 2 Guests
Fantastic Orleans Waterfront 2BR Cottage
9.8 (17 Reviews)
2 Bedrooms 5 Guests
Cozy Cottage Overlooking Rock Harbor Creek
9.8 (10 Reviews)
1 Bedroom 4 Guests
Minutes to Oceanside Beaches
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9.4 (9 Reviews)
3 Bedrooms 6 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
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
FromGB £671 per night
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9.0 (3 Reviews)
4 Bedrooms 8 Guests
Great Home with Game Space Close to Baech
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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
FromGB £498 per night
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9.0 (2 Reviews)
4 Bedrooms 6 Guests
Clean and Quiet North Eastham Cottage Near Beaches
9.6 (20 Reviews)
3 Bedrooms 6 Guests
Pine Grove Cottage
FromGB £89 per night
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9.0 (2 Reviews)
2 Bedrooms 2 Guests
Amazing Outdoor Space Access to Town Cove
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9.0 (1 Review)
5 Bedrooms 12 Guests

About First Encounter Beach Vacation Rentals

With more than 919 First Encounter Beach vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in First Encounter Beach.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner First Encounter Beach, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in First Encounter Beach. Places to stay near First Encounter Beach are 1107.41 ft² on average, with prices averaging GB £450 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in First Encounter Beach with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About First Encounter Beach?

What are the top vacation rentals in First Encounter Beach?

How many Rentbyowner vacation rentals are available in First Encounter Beach?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 919 in the First Encounter Beach area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in First Encounter Beach. 

Nearby Neighborhood (4)

NeighborhoodProperty Count
Indian Neck Heights Vacation Rentals in Eastham, Massachusetts 25
West Brewster Vacation Rentals in Eastham, Massachusetts 544
Pleasant Point Vacation Rentals in Eastham, Massachusetts 651
Sea Pines Vacation Rentals in Eastham, Massachusetts 701