Shelter Island Boutique Hotels

The Menhaden Hotel

Hotel

207 Front Street, Greenport, NY 11944, USA

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Rooftop Lounge & Bar
Sustainable Luxury
Culinary Delights

5 Baths 310 ft²

Faraway Sag Harbor

Hotel

31 W. Water Street, Sag Harbor, NY 11963, USA

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Romantic Oasis
Culinary Delights
Total Relaxation

3 Baths 401.49 ft²

Topping Rose House

Hotel

1 Bridgehampton Sag Harbor Turnpike, Bridgehampton, NY 11932, USA

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Spa Breaks
Foodies
Romantic Break

7 Baths 496.68 ft²

Southampton Inn

Hotel

91 Hill Street, Southampton, NY 11968, USA

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Romantic Getaways
Culinary Delights
Wellness & Relaxation

12 Baths 3296.45 ft²

Journey East Hampton

Hotel

490 Pantigo Road, East Hampton, NY 11937, USA

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Boutique Beach Life
Romantic Breaks
Active Holiday

4 Baths 371.36 ft²

The Roundtree, Amagansett

Hotel

273 Main Street, PO box 799, Amagansett, NY 11930, USA

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Total Relaxation
Romantic Break
Boutique

8 Baths 680.82 ft²

The Griswold Inn

Hotel

36 MAIN ST, Essex, CT 06426, USA

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Historic Charm
Culinary Delights
Intimate Atmosphere

3 Baths 221.73 ft²

Madison Beach Hotel, Curio Collection by Hilton

Hotel

94 W Wharf Rd, Madison, CT 06443-2905, USA

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Romantic Escape
Total Relaxation
Spa Breaks

5 Baths 301.39 ft²

Gurney's Montauk Resort & Seawater Spa

Resort

290 Old Montauk Highway, Montauk, NY 11954, USA

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Total Relaxation
Romantic Break
Spa Breaks

13 Baths 500.26 ft²

The Quogue Club

Hotel

47 Quogue Street, Quogue, NY 11959, USA

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Romantic Break
Spa Breaks
Local Exploring

5 Baths 275.56 ft²

The Griswold Inn

36 MAIN ST, Essex, CT 06426, United States of America

8.6

254 reviews

From $255

Guest Review: Felt like being brought back in time in the America ambience. The restaurant and Tap Room with music and great food.

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Southampton Inn

91 Hill Street, Southampton, NY 11968, United States of America

8.5

162 reviews

From $483

Guest Review: I have stayed at many places in Southampton. This place was great. Parking right out front. Rooms are large bright and clean. Bathroom is a good size. Beds very comfortable and nice bedding. Water and coffee maker. Toiletries. Lobby with fireplace and staff very friendly. Walking distance to everything in Southampton. It was a pleasure.

31 W. Water Street, Sag Harbor, NY 11963, United States of America

8.8

143 reviews

From $920

Guest Review: I was at Baron's Cove for a short 1 day visit with my daughter to attend a local event. Staff was excellent; both over the phone and in person. They went above and beyond to make sure that my room was available for an early check in. The room and all amenities were great and well thought of. The room decor was cute and the room didn't smell like a musty hotel. The bed was super comfortable. I would definitely recommend Baron's Cove to anyone wanting a nice getaway.

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For family-friendly stays, consider The Menhaden Hotel, which offers spacious rooms and a central location. Another great option is Baron's Cove, featuring family-oriented activities and amenities that cater to both parents and kids.

Yes! For a romantic getaway, check out Topping Rose House, known for its intimate atmosphere and luxurious spa services. Alternatively, Gurney's Montauk Resort & Seawater Spa provides stunning views and a tranquil setting, making it ideal for couples.

If you're seeking luxury, look no further than The Griswold Inn for its elegant design and upscale dining. Another exceptional choice is The Quogue Club, offering opulent accommodations and personalized service in a sophisticated environment.

Food lovers will delight in staying at Topping Rose House, where farm-to-table cuisine takes center stage. Additionally, Journey East Hampton features a renowned restaurant with a focus on fresh, local ingredients, making it a foodie favorite.

Travelers on a budget will find value at Southampton Inn, which combines affordability with comfort and convenience. Another great option is The Roundtree, Amagansett, offering modern charm without breaking the bank.