Vacation rentals in Gardiners Bay

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Top-rated vacation rentals in Gardiners Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 193 reviews

Huge Island Getaway Pool HotTub Walk To Beach

Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.

Oct 21 – 28

G$209,374 GYD per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

Feb 3 – 10

G$114,284 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Oct 20 – 27

G$136,614 GYD per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's, and recently & lovingly fully renovated and restored. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Nov 5 – 12

G$90,183 GYD per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

Walk to the beach at Black Point, Niantic, Ct

Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Mar 2 – 9

G$31,711 GYD per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 48 reviews

Hampton Springs by Summer | Open Breezy Bungalow

Our updated, airy bungalow in the Springs neighborhood of East Hampton is located minutes away from Clearwater Beach. The community is full of history, surreal bay beaches, dining, shopping & more. You will have the best of both worlds– being near all this prestigious community has to offer, while also being set in a quiet residential neighborhood. Enjoy high-speed WiFi, luxury furnishings, thoughtful amenities, Smart TV, and beach essentials in our retreat from the city.

Dec 10 – 17

G$137,760 GYD per night

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - Apt #1

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Jan 3 – 10

G$25,437 GYD per night

Guest favorite

Guest suite in East Hampton

4.89 out of 5 average rating, 222 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Sep 27 – Oct 4

G$55,992 GYD per night

Superhost

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

Oct 3 – 10

G$157,152 GYD per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Enjoy this centrally-located historic home restored w/ modern conveniences. 1st FL includes sunny living room w/ comfortable seating and smart TV; full eat-in modern kitchen; mudroom and powder room. 2nd FL has two spacious bdrms each with full ensuite bathrooms. Short walk to LIRR, Shelter Island Ferry and Jitney stop, steps from vibrant Front and Main Street shops, restaurants and beach.

Oct 30 – Nov 6

G$117,318 GYD per night

Guest favorite

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 227 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

Apr 21 – 28

G$149,830 GYD per night

Guest favorite

Home in East Hampton

5.0 out of 5 average rating, 13 reviews

Historic East Hampton Home - Private Beach Access

Experience breathtaking sunset views over the harbor from our beautiful mid-century modern home. Designed by Kaneji Domoto, a student of Frank Lloyd Wright, the house seamlessly blends with its stunning surroundings, offering abundant natural light and water views from nearly every room.

Feb 5 – 12

G$114,705 GYD per night