First Encounter Beach Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes 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
Whalewalk Inn and Spa
FromR4,853 per night
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10.0 (87 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 Parsonage Inn
FromR4,074 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
Truly Wonderful Cape Cottage
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 Inn at the Oaks
FromR4,436 per night
9.2 (322 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
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 (27 Reviews)
2 Bedrooms 4 Guests
Beach Getaway with Private Backyard
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10.0 (1 Review)
4 Bedrooms 10 Guests
The Breeze on Minister's Pond
10.0 (25 Reviews)
1 Bedroom 2 Guests
3000 Sq Ft Home with Hot Tub
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10.0 (1 Review)
3 Bedrooms 8 Guests
The Pet-Friendly Surf Shack Hideaway on the Cove
10.0 (23 Reviews)
2 Bedrooms 7 Guests
Newly updated spacious steps to water
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10.0 (1 Review)
2 Bedrooms 4 Guests
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
10.0 (19 Reviews)
2 Bedrooms 6 Guests
2 Miles to Nauset & Coast Guard Beach Dog Friendly
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10.0 (1 Review)
6 Bedrooms 12 Guests
Cape Cod Sunscape. Orleans
10.0 (17 Reviews)
2 Bedrooms 6 Guests
Half Mile to Private Association Beach
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10.0 (1 Review)
2 Bedrooms 5 Guests
Beach and Golf Hub with All-Season Sunroom in Cape Cod
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10.0 (1 Review)
5 Bedrooms 9 Guests
Cape Cod Cottage Retreat
10.0 (15 Reviews)
2 Bedrooms 4 Guests
The Parsonage
FromR6,379 per night
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9.8 (9 Reviews)
10 Bedrooms 22 Guests
New Eastham Oceanside Guest Suite with Pool and Hot Tub
10.0 (15 Reviews)
1 Bedroom 2 Guests
The Tranquil Heron Cottage
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9.8 (5 Reviews)
1 Bedroom 6 Guests
Steps to Rock Harbor, Fully Renovated Cape Cod Cottage
10.0 (9 Reviews)
2 Bedrooms 6 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 (8 Reviews)
2 Bedrooms 6 Guests
🐚The Bay Cottage on Thumpertown Beach
9.8 (11 Reviews)
2 Bedrooms 4 Guests
Beautiful Spacious Family Retreat w Pool
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
The Seagrove Suites & Guest Rooms
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9.2 (127 Reviews)
1 Bedroom 2 Guests
Cozy Cottage Overlooking Rock Harbor Creek
9.8 (10 Reviews)
1 Bedroom 4 Guests
4 Bedroom Home by Leavetown Vacations
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9.7 (3 Reviews)
4 Bedrooms 8 Guests
Eagle Wing Inn - Cape Cod
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9.8 (425 Reviews)
1 Bedroom 2 Guests
Newly Renovated Cottage on Town Cove!
9.8 (9 Reviews)
2 Bedrooms 4 Guests
Inn at the Oaks
FromR6,459 per night
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9.6 (34 Reviews)
13 Bedrooms 31 Guests
Olde Tavern Motel And Inn
9.4 (237 Reviews)
1 Bedroom 2 Guests
Bike to Nauset Beach or Walk to Mill Pond
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9.5 (11 Reviews)
3 Bedrooms 6 Guests
Private Road - Near Bike Trail & Beaches
9.6 (35 Reviews)
2 Bedrooms 4 Guests
Great Location Near Cape Cod National Seashore
9.6 (33 Reviews)
2 Bedrooms 4 Guests
Minutes to Oceanside Beaches
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9.4 (9 Reviews)
3 Bedrooms 6 Guests
Walk to Campground Beach Modern, Well‑Kept Cottage
9.6 (29 Reviews)
2 Bedrooms 4 Guests
Four Season Modern Cape Cod Cottage (with heat)
9.4 (6 Reviews)
2 Bedrooms 4 Guests
Beachfront on Cape Cod Bay in Eastham! (1039)
9.6 (24 Reviews)
2 Bedrooms 6 Guests
Perfect Relaxation Spot 5 min to Beach
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9.4 (5 Reviews)
3 Bedrooms 8 Guests
Clean and Quiet North Eastham Cottage Near Beaches
9.6 (20 Reviews)
3 Bedrooms 6 Guests
Waterfront amazing views near beaches
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9.3 (3 Reviews)
3 Bedrooms 6 Guests
Steps to Skaket Beach
FromR14,939 per night
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9.0 (3 Reviews)
4 Bedrooms 8 Guests
🐳 The Whale Song - Dog-Friendly Studio
9.6 (14 Reviews)
1 Bedroom 2 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
Eastham Cottage with AC and Private Back Yard (2217)
9.6 (10 Reviews)
2 Bedrooms 4 Guests
Gray Gables
FromR11,097 per night
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9.0 (2 Reviews)
1 Bedroom 6 Guests

About First Encounter Beach Vacation Rentals

With more than 956 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 1110.46 ft² on average, with prices averaging R10,137 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 956 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
Pleasant Point Vacation Rentals in Eastham, Massachusetts 687
West Brewster Vacation Rentals in Eastham, Massachusetts 574
Sea Pines Vacation Rentals in Eastham, Massachusetts 725