First Encounter Beach Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes 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
FromR4,876 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
FromR4,073 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
The Parsonage
FromR6,377 per night
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10.0 (4 Reviews)
10 Bedrooms 22 Guests
The Inn at the Oaks
FromR4,434 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
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
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 First Encounter Beach Vacation Rentals

With more than 969 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 1160.21 ft² on average, with prices averaging R10,143 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 969 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 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