Shelter Island
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Featured Condos in Shelter Island

The Surf Club
3.5 out of 5
20 Surfside Avenue, Montauk, NY
AU$262
per night
10 Nov. - 11 Nov.

Nestled on the beach, this Montauk condo is within a 10-minute walk of South Edison Beach and Fort Pond. Kirk Park Beach and Shadmoor State Park are also within ...

4.2/5Very Good! (135 reviews)

"Clean well maintained rooms and property with great views of the ocean and quick walk to town. Have stayed here a number of times and always a good experience."…"

Reviewed on 21 Oct. 2019

The Surf Club
Cliffside Resort Condominiums
3 out of 5
61475 Route 48 (North Road), Greenport, NY
AU$428
per night
3 Nov. - 4 Nov.

Offering direct access to the beach, this Greenport condo is within 3 mi (5 km) of 67 Steps Beach, Norman E. Klipp Marine Park and Island's End Golf and Country ...

4.4/5Wonderful! (80 reviews)

"Courteous staff. All facilities very clean Grounds pristine. Well equipped units"…"

Reviewed on 27 Sep. 2019

Cliffside Resort Condominiums
Beach Plum Resort
3 out of 5
779 Old Montauk Highway, Montauk, NY
AU$245
per night
24 Oct. - 25 Oct.

With direct access to the beach, this Montauk condo is within a 10-minute walk of Second House Museum, Kirk Park Beach and Fort Pond. South Edison Beach and ...

4.2/5Excellent! (83 reviews)

"Resort was great, pool was fantastic, unit needed updating. Would definitely stay there again, just NOT in Unit 7"…"

Reviewed on 2 Oct. 2019

Beach Plum Resort
Driftwood Resort
3.5 out of 5
2178 Montauk Highway, Montauk, NY
AU$252
per night
29 Oct. - 30 Oct.

Nestled on the beach, this Montauk condo is within 1 mi (2 km) of Napeague State Park and Walking Dunes Trailhead. Hither Woods Preserve is 1.8 mi (3 km) ...

4.2/5Excellent! (99 reviews)

"Beautiful! My favorite place to stay in! Super clean!"…"

Reviewed on 9 Sep. 2019

Driftwood Resort
The Montauk Soundview
3 out of 5
6 Soundview Drive, Montauk, NY
Get Rates

Nestled on the beach, this Culloden Shores condo is within a 15-minute walk of Montauk Marine Basin and Gin Beach. Fort Pond Bay Beach and Ditch Plains Beach ...

4.2/5Very Good! (37 reviews)

"We had an issue with our stay, but the host and manager responded very quickly and we had a lovely stay."…"

Reviewed on 21 Oct. 2019

The Montauk Soundview
Born Free Suites by the Sea
3 out of 5
115 South Emerson Avenue, Montauk, NY
AU$193
per night
28 Oct. - 29 Oct.

Situated near the beach, this condo is steps away from South Edison Beach and Fort Pond. Kirk Park Beach and Second House Museum are also within 15 minutes. ...

4.1/5Very Good! (84 reviews)

"The towels are old and were a little dirty, something to invest in for the company. Room was a good size, conveniant location. Bed was ok, a little springy feeling. This just felt a little old and run down but overall we enjoyed our stay."…"

Reviewed on 9 Sep. 2019

Born Free Suites by the Sea
The Hermitage
3.5 out of 5
2148 Montauk Highway, Amagansett, NY
AU$174
per night
27 Oct. - 28 Oct.

Nestled on the beach, this Amagansett condo is within a 15-minute walk of Napeague State Park and Walking Dunes Trailhead. Hither Woods Preserve is 1.8 mi (3 ...

4.6/5Wonderful! (65 reviews)

"We had a lovely stay! There were a lot of family and kids here but it wasn't overcrowded. The pool, gym, and beach are all kept in great shape, and the staff was all very friendly and helpful throughout our stay. We will be coming back!"…"

Reviewed on 30 Jun. 2019

The Hermitage
Breakers Montauk
3 out of 5
769 Old Montauk Highway, Montauk, NY
AU$428
per night
25 Oct. - 26 Oct.

Situated in Montauk, this beach condo is within a 10-minute walk of Second House Museum, Fort Pond, and Kirk Park Beach. South Edison Beach and Fort Pond Bay ...

3.8/5Good! (30 reviews)

"Great stay! Staff is very friendly and helpful, rooms were updated/clean/super cute, and food at the cafe was great. Only complaint was that we wished there were more mirrors in the room or at least a full length mirror :)"…"

Reviewed on 3 Jun. 2019

Breakers Montauk
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Shelter Island

Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
AU$406
per night
27 Oct. - 28 Oct.
4.3/5Excellent! (301 reviews)

"Amazing property. Went on a whim to celebrate an anniversary. The staff bent over backwards to accommodate our request for another room. Our original room had an obstructed view of the ocean due to a tent being placed for an event. They quickly moved us to another room with a stunning view of the ..."…"

Reviewed on 9 Sep. 2019

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
AU$277
per night
30 Oct. - 31 Oct.
4.2/5Excellent! (356 reviews)

"Beautiful property and well manicured landscaping. Very relaxing here love it!!!!!!"…"

Reviewed on 20 Oct. 2019

Water's Edge Resort & Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
AU$135
per night
28 Oct. - 29 Oct.
4.4/5Excellent! (125 reviews)

"The property was beautiful yet the room had a faint smell of cigarette smoke."…"

Reviewed on 16 Oct. 2019

Montauk Manor
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.