Shelter Island Hotels

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Nov 20 - Nov 21
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Top 10 trending Shelter Island hotels

Front of property - evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is P8,168
P10,485 total
includes taxes & fees
Dec 1 - Dec 2
Montauk Manor
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4.0 star property
Montauk
8.2 out of 10, Very Good, (691)
"Beautiful view and accomodations. Enjoyed the bathhouse and hotel amenities"
United States
Alex
The price is P15,380
P20,992 total
includes taxes & fees
Dec 4 - Dec 5
Gurney's Montauk Resort & Seawater Spa
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 star property
Old Saybrook Center
9.4 out of 10, Exceptional, (1005)
"Beautiful property, we loved our room, friendly staff. "
United States
Natalie
The price is P14,283
P17,900 total
includes taxes & fees
Nov 30 - Dec 1
Saybrook Point Resort & Marina
In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2.0 star property
Hampton Bays
7.2 out of 10, Good, (67)
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1004)
"We love the stay everything was perfect"
United States
angelica
The price is P9,446
P11,880 total
includes taxes & fees
Dec 7 - Dec 8
Water's Edge Resort & Spa
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
7.2 out of 10, Good, (969)
"Love the area love the room size clean parking was perfect "
United States
Sherwood
The Atlantic Hotel
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2.0 star property
Saybrook Manor
8.0 out of 10, Very Good, (1000)
"Always a great stay at Pier Blue. Comfy bed and plenty of room."
United States
Patricia
Pier Blue Inn Old Saybrook - Essex
Exterior
Zey Hotel

Zey Hotel

3.5 star property
Greenport
9.2 out of 10, Wonderful, (288)
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
View from room
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (535)
"Amazing property, rooms, and staff. Book a room with a balcony for amazing views!"
United States
Matthew
The price is P6,153
P9,917 total
includes taxes & fees
Dec 21 - Dec 22
The Harbor Front Inn
Exterior
Madison Beach Hotel

Madison Beach Hotel

4.0 star property
Madison Center
9.4 out of 10, Exceptional, (337)
"Staff and hotel are lovely "
United States
Steven
The price is P14,448
P16,615 total
includes taxes & fees
Dec 1 - Dec 2
Madison Beach Hotel
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
7.8 out of 10, Good, (1008)
"Staff was kind. Easy, comfortable stay."
United States
Jake
The price is P5,961
P6,855 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn Old Saybrook - Westbrook
Property grounds
The Hampton Maid

The Hampton Maid

2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (683)
"Was so lovely would definitely come back again, very cute clean and safe "
United Kingdom
Maria
The Hampton Maid
1 bedroom, premium bedding, pillowtop beds, blackout drapes
Offshore Montauk

Offshore Montauk

2.0 star property
Montauk
9.4 out of 10, Exceptional, (69)
"Excellent stay! Gorgeous views, very clean rooms, helpful staff and beautifully done. Will stay again!"
United States
Erica
The price is P4,789
P8,838 total
includes taxes & fees
Dec 3 - Dec 4
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, sun loungers
Marram

Marram

4.0 star property
Montauk
8.8 out of 10, Excellent, (249)
"It was an amazing relaxing weekend. We want to come back next year the same weekend!"
United States
Piera
The price is P10,109
P23,332 total
includes taxes & fees
Nov 24 - Nov 25
Marram
Front of property
The Preston House & Hotel

The Preston House & Hotel

3.5 star property
Riverhead
9.8 out of 10, Exceptional, (368)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is P11,026
P12,597 total
includes taxes & fees
Dec 4 - Dec 5
The Preston House & Hotel
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (569)
"We had lovely stay, the staff was knowledgeable, efficient, and friendly. Will visit again! "
United States
Lori
The price is P11,097
P12,678 total
includes taxes & fees
Nov 23 - Nov 24
Sag Harbor Inn
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (437)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is P6,046
P7,814 total
includes taxes & fees
Nov 21 - Nov 22
Hamlet Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (382)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is P7,610
P8,754 total
includes taxes & fees
Nov 24 - Nov 25
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
8.6 out of 10, Excellent, (593)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is P9,446
P13,676 total
includes taxes & fees
Nov 23 - Nov 24
Sound View Greenport
Exterior
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (207)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
The price is P10,024
P13,809 total
includes taxes & fees
Nov 23 - Nov 24
The Sagaponack
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.
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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Learn more about Shelter Island

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset Beach.

Coecles Harbor

When in Coecles Harbor, you can plan a visit to Shelter Island Whale's Tail and Gardiner's Bay Country Club, some noteworthy sights in the nearby area.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Shorewood

While there might not be top attractions in Shorewood, you can explore the larger area and discover places like Mashomack Preserve and Shelter Island Historical Society.

Hay Beach

Hay Beach might not have many top sights, but Gardiner's Bay Country Club and Greenport Carousel are two attractions nearby that you can check out.

Stay near popular Shelter Island attractions

Colorful pebbles and shells on a beach

Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties
Man watching sailboat on Long Island Sound

Wades Beach

Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
Central Park summer

Top Shelter Island Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"The staff is very nice. The pool was very clean and the room was in perfect condition. I will stay here again."
Robert 1-night trip
Posted 4 days ago
Quality Inn Old Saybrook - Westbrook

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
Get rates
7.8/10 Good! (1,002 reviews)

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 18.4 mi (29.7 km) from the heart of Shelter Island, Gurney's Montauk Resort & Seawater Spa is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Pier Blue Inn Old Saybrook - Essex and Montauk Blue Hotel. See all available top hotels, or vacation rentals in Shelter Island.
If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?
Yes, the majority of hotel room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.
What's the best pet-friendly accommodation in Shelter Island?
Sunset Beach Hotel is a top hotel for people traveling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.
What's the best place to stay near the beach in Shelter Island?
Sunset Beach Hotel is a top beachfront hotel with free WiFi and free parking, and it's located on Sunset Beach. See more stays near the beach in Shelter Island.
What are some accommodations with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Blue Hotel and Quality Inn Old Saybrook - Westbrook are a couple of other choices that feature an onsite pool. View all hotels with pools in Shelter Island.
What's it like to stay in Shelter Island?
Visitors can enjoy all that Shelter Island has to offer including the parks, beaches, and museums. This city also attracts tourists with its scenic landscape. In Shelter Island, there are 95 hotels and other accommodations to choose from. Find out more about Shelter Island.
What should I see while I'm in Shelter Island?
Natural beauty is on display at Sunset Beach, Mashomack Preserve, and Crescent Beach. A couple of additional sights to add to your agenda are Gardiner's Bay Country Club and Shelter Island Historical Society. Check out what more to see and do in Expedia's Shelter Island guide.
What's the weather like in Shelter Island?
The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.

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