Vacation rentals in Gardiners Island

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Top-rated vacation rentals in Gardiners Island

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Guest favourite

Cabin in Montauk

4.96 out of 5 average rating, 424 reviews

Montauk | Tiny Cottage in Private Hither Woods

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Oct. 22 – 29

$459 CAD per night

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Meticulously cleaned home. Tranquil family neighborhood in historic artist's beach community. Wood burning fireplace. Private fenced-in backyard . Heated saltwater pool in summer. Half mile to private bay beach, bike great trails & savor delicious meals prepared in fully equipped kitchen. Don’t miss Clearwater Beach's stunning sunset. Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby. Smoke free.Small dogs permitted.Rental Registry 23-625.

Sep. 19 – 26

$860 CAD per night

Guest favourite

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.

Mar. 10 – 17

$1,232 CAD per night

Guest favourite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Aug. 28 – Sep. 4

$595 CAD per night

Guest favourite

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.

Jan. 9 – 16

$248 CAD per night

Guest favourite

Cottage in Groton

4.94 out of 5 average rating, 139 reviews

EASY BEAT

LOVELY MID 1800'S COTTAGE Located in the historic Groton Bank neighborhood. Close to beaches, casinos, walking distant to EB. Short drive to Pfizer, Coast Guard Academy, Connecticut College, US Submarine Base and minutes to downtown Mystic. This property is a one bedroom one bath with a single pullout couch in bedroom and living room. Offers a spacious outside lawn with patio. Lots of off street parking. Fenced yard for pets. New Central Air and heat. Washer, dryer, grill and fire pit.

Feb. 19 – 26

$242 CAD per night

Guest favourite

Apartment in New London

4.98 out of 5 average rating, 289 reviews

Quiet Neighborhood home close to everything

Spacious & charming 2 bed RM APT on the 3rd fl of my home, gives you all the comforts of home while you’re away. We are a quick walk to L&M (Yale) Hospital, Mitchell College, And EB NL Campus. Short drive to the Coast Guard Academy, Conn College, Domion (Millstone) and The US Submarine Base. And if you’re here for fun, we are 1.5 miles to Ocean Beach (borrow our pass for free access) 20 min to Mohegan Sun & 25 to Foxwoods and 15 min to Mystic. Follow us on Insta at 199Thames.

Mar. 7 – 14

$240 CAD per night

Guest favourite

Guesthouse in East Hampton

4.86 out of 5 average rating, 21 reviews

Private Springs Cottage & Porch

Find your peace in this newly renovated private cottage getaway. Perfect for a couple looking to hit the beaches and enjoy stunning sunsets at the bay. Next to the main house, the cottage has a private entrance, mini kitchen (not full), and an indoor / outdoor bathroom. A large screened in porch offers a quiet space to have your coffee, do yoga and play ping pong! Backyard with fire pit, BBQ & hammock. Blow up mattress available for child. Local sunset restaurants minutes away.

Jun. 26 – Jul. 3

$586 CAD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

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. 14 – 21

$188 CAD per night

Guest favourite

Cottage in Waterford

4.99 out of 5 average rating, 107 reviews

Coastal Cottage Private Studio

Beautiful coastal studio cottage located on the shoreline of CT. Your cottage is spacious and private with keyless entry and private dedicated parking. Originally an art studio, this recently renovated cottage is one mile to the beaches and local attractions. Our cottage is popular among Connecticut College, Coast Guard Alumni/parents and for anniversary celebrations! Enjoy...Now you can kick back and relax... you've found your home away from home! 🤩🏡 😊

Oct. 7 – 14

$310 CAD per night

Guest favourite

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

May 16 – 23

$380 CAD per night

Guest favourite

Guesthouse in Mystic

4.99 out of 5 average rating, 541 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Dec. 27 – Jan. 1

$305 CAD per night