First Encounter Beach Vacation Rentals

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

Waterfront Cottage - Adorable & Private
10.0 (82 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
FromAU $436 per night
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10.0 (92 Reviews)
1 Bedroom 2 Guests
Seaside Retreat w Private Beach Landing
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10.0 (4 Reviews)
3 Bedrooms 6 Guests
The Parsonage Inn
FromAU $353 per night
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9.8 (35 Reviews)
1 Bedroom 2 Guests
Waterfront, Modern, On a Pond for Boating and Swimming
10.0 (2 Reviews)
2 Bedrooms 5 Guests
The Parsonage
FromAU $553 per night
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10.0 (4 Reviews)
10 Bedrooms 22 Guests
The Inn at the Oaks
FromAU $384 per night
9.2 (322 Reviews)
1 Bedroom 2 Guests
Waterside Eastham Cottage with Quintessential Cape Cod Charm
10.0 (1 Review)
2 Bedrooms 4 Guests
Beach Getaway with Private Backyard
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10.0 (2 Reviews)
4 Bedrooms 10 Guests
Skaket Beach Area Dream
FromAU $1,932 per night
New
1 Bedroom 9 Guests
4-5 Min to Mill Pond or Nauset Beach
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10.0 (2 Reviews)
4 Bedrooms 9 Guests
Lovely House 5 Min to Beach with Deck Grill and Garage
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10.0 (2 Reviews)
4 Bedrooms 8 Guests
New 2026 3BD Home With Guest House
New
4 Bedrooms 8 Guests
Dog Friend Waterfront Home
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10.0 (2 Reviews)
2 Bedrooms 4 Guests
Waterfront Fun at this Huge Family Estate
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10.0 (1 Review)
11 Bedrooms 23 Guests
Truly Wonderful Cape Cottage
FromAU $423 per night
10.0 (135 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 (61 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 Modern, Well‑Kept Cottage
10.0 (51 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 (41 Reviews)
2 Bedrooms 5 Guests
3000 Sq Ft Home with Hot Tub
FromAU $1,432 per night
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10.0 (1 Review)
3 Bedrooms 8 Guests
Great Waterfront Property, Kayak the National Park Seashore
10.0 (37 Reviews)
2 Bedrooms 6 Guests
3 Bicycles Provided! Cape Cod Cottage w/Deck
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10.0 (1 Review)
3 Bedrooms 6 Guests
Oceanfront w/Private Stairs to Beach and Spectacular Sunsets!
10.0 (28 Reviews)
2 Bedrooms 4 Guests
Minutes to Private Association
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10.0 (1 Review)
4 Bedrooms 8 Guests
The Breeze on Minister's Pond
10.0 (26 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 (20 Reviews)
2 Bedrooms 5 Guests
Half Mile to Private Association Beach
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10.0 (1 Review)
2 Bedrooms 5 Guests
New Eastham Oceanside Guest Suite with Pool and Hot Tub
10.0 (20 Reviews)
1 Bedroom 2 Guests
Cape Cod Sunscape. Orleans
FromAU $1,173 per night
10.0 (17 Reviews)
2 Bedrooms 6 Guests
Cape Cod Cottage Retreat
FromAU $568 per night
10.0 (16 Reviews)
2 Bedrooms 4 Guests
1940s Cottage Stunner Large Studio w/loft feel dog friendly
9.8 (23 Reviews)
1 Bedroom 3 Guests
Beach & Golf Hub w/All-Season Sunroom in Cape Cod
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10.0 (1 Review)
5 Bedrooms 9 Guests
The Seagrove Suites & Guest Rooms
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9.2 (128 Reviews)
1 Bedroom 2 Guests
Fantastic Orleans Waterfront 2BR Cottage
9.8 (17 Reviews)
2 Bedrooms 5 Guests
Minutes to Oceanside Beaches
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9.8 (13 Reviews)
3 Bedrooms 6 Guests
Eagle Wing Inn - Cape Cod
FromAU $478 per night
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9.8 (441 Reviews)
1 Bedroom 2 Guests
Castaway Cottage on the bay~Dog Friendly Too!
9.8 (16 Reviews)
2 Bedrooms 5 Guests
The Tranquil Heron Cottage
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9.8 (5 Reviews)
3 Bedrooms 6 Guests
Olde Tavern Motel And Inn
FromAU $395 per night
9.4 (253 Reviews)
1 Bedroom 2 Guests
🐚The Bay Cottage on Thumpertown Beach
9.8 (13 Reviews)
2 Bedrooms 4 Guests
Inn at the Oaks
FromAU $560 per night
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9.7 (36 Reviews)
13 Bedrooms 31 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
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
Beachfront on Cape Cod Bay in Eastham! (1039)
9.6 (24 Reviews)
2 Bedrooms 6 Guests
Four Season Modern Cape Cod Cottage (with heat)
9.4 (6 Reviews)
2 Bedrooms 4 Guests
Clean and Quiet North Eastham Cottage Near Beaches
9.6 (20 Reviews)
3 Bedrooms 6 Guests
Perfect Relaxation Spot 5 min to Beach
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9.4 (5 Reviews)
3 Bedrooms 8 Guests
Waterfront amazing views near beaches
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9.3 (3 Reviews)
3 Bedrooms 6 Guests
🐳 The Whale Song - Dog-Friendly Studio
9.6 (14 Reviews)
1 Bedroom 2 Guests
Steps to Skaket Beach
FromAU $1,295 per night
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9.0 (3 Reviews)
4 Bedrooms 8 Guests
Newly Renovated Cottage on Town Cove!
9.6 (10 Reviews)
2 Bedrooms 4 Guests
Gray Gables
FromAU $962 per night
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9.0 (3 Reviews)
4 Bedrooms 6 Guests

About First Encounter Beach Vacation Rentals

With more than 973 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 1162.54 ft² on average, with prices averaging AU $897 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 973 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
West Brewster Vacation Rentals in Eastham, Massachusetts 575
Indian Neck Heights Vacation Rentals in Eastham, Massachusetts 688
Pleasant Point Vacation Rentals in Eastham, Massachusetts 705
Sea Pines Vacation Rentals in Eastham, Massachusetts 750