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Thimble Islands island rentals

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Top-rated island rentals in Thimble Islands

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

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Island in Glocester

4.81 out of 5 average rating, 140 reviews

Rustic Private Island Cabin on Lake

(No running water or electricity) cabin on private island. Sleeps 11. Propane stovetop. dishes, cutlery, pots and pans in cabin. Fire pit, wood burning stove, wood available for purchase. Rowboat for transportation, for you to row to and from the island. Flush toilet (bucket of water from the lake). Skylights, some solar lights. Ample parking. Bring AA or AAA batteries for lighting. Best to bring your own flashlights or battery lanterns. 10 pm noise curfew. Arrival after 2 pm, leave by 11am.

Island in East Hampton

An Island for Rent for Up To 39 People

A Private Island for Rent It's all Lakefront Laurel Island is a five acre Island on a lake in Connecticut. Laurel Island is a perfect location to hold a retreat, reunion, or family group that combines the privacy and peacefulness of an Island and facilities for groups both large and small. Accoommodations include 5 private cottages and a large main Lodge for gathering. Local catering is available for group meals . The five acre Island has canopy trees, blueberry bushes, rocky outcrops

Island in East Hampton

Private Island on a Lake Sleeps 39

This private Island is available to rent. You can rent the entire Island or just a cabin or two. We take you to the Island on our pontoon boat and while on the Island you can share the use of our canoes, kayaks, standup boards or paddle boats. There is also volleyball, badminton, horseshoes on the Island. There are five cabins and a Lodge that can be rented together or separately.

Vacation rentals for every style

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Houses

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Thimble Islands vacation rentals

Laptop-friendly workspace

Air conditioning

Thimble Islands vacation rentals

Home in Branford

4.91 out of 5 average rating, 379 reviews

Adorable Beach House on the Long Island Sound

Cottage in Clinton

4.87 out of 5 average rating, 404 reviews

Shalom Cottage with beach rights.

Home in East Haven

4.88 out of 5 average rating, 200 reviews

Beach Cottage by the Sea

Cabin in East Haddam

4.91 out of 5 average rating, 412 reviews

Getaway Machimoodus - NYC/Boston

Rental unit in New Haven

4.96 out of 5 average rating, 249 reviews

Urban Sanctuary

Guest suite in Wallingford

5 out of 5 average rating, 509 reviews

Wintergreen Gardens Suite @ William Becroft House

Guest suite in New Haven

4.99 out of 5 average rating, 161 reviews

Cozy cottage in historic neighborhood

Guesthouse in Guilford

4.99 out of 5 average rating, 458 reviews

Get Back to Nature at a Modern Wood Clad Getaway

Thimble Islands house rentals

Home in East Haven

4.95 out of 5 average rating, 103 reviews

The Breakaway - a waterfront gem.

Home in Cheshire

5 out of 5 average rating, 120 reviews

Pool House

Home in New Haven

5 out of 5 average rating, 205 reviews

Q River House - 2 bdrm, minutes from Yale/Downtown

Home in Stony Brook

4.94 out of 5 average rating, 488 reviews

Spacious Studio Apartment- near SBU

Home in East Haddam

4.94 out of 5 average rating, 107 reviews

Romantic Getaway at The Lake!

Home in Preston

4.96 out of 5 average rating, 611 reviews

Entire House Magical Waterfront Getaway

Home in Milford

4.99 out of 5 average rating, 244 reviews

The Daydreamer -Walk to Walnut Beach, Pet Friendly

Home in Wilton

4.93 out of 5 average rating, 162 reviews

Mid Century Modern Cottage

Other great vacation rentals in Thimble Islands

Rental unit in West Haven

4.9 out of 5 average rating, 434 reviews

! ! ! entire apartment close to the beach ! !

Cabin in Rocky Point

4.9 out of 5 average rating, 407 reviews

Great little place just for a couple

Rental unit in New Haven

4.92 out of 5 average rating, 154 reviews

Tranquil Apartment with Waterview, Walk to Beach!

Guest suite in Hamden

4.96 out of 5 average rating, 723 reviews

Large Private Studio + Entrance + Bath

Guest suite in Stonington

4.99 out of 5 average rating, 155 reviews

Morgan Suite

Guest suite in Cutchogue

4.88 out of 5 average rating, 595 reviews

Walk to Vineyards, Beaches, Farms & Town

Cottage in Westbrook

4.85 out of 5 average rating, 102 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

Rental unit in East Haddam

4.89 out of 5 average rating, 114 reviews

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