Book Cheap Hotels in Shelter Island
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Most frequently booked Shelter Island hotels

Montauk Manor
236 Edgemere St., Montauk, NY
32.71 km from city centre
The price is CA $188 per night
CA $188
CA $243 total
includes taxes & fees
25 Mar - 26 Mar
Stay at this 3.5-star aparthotel in Montauk. Enjoy free WiFi, an outdoor pool, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Montauk Point and Shadmoor State Park are located nearby.
Pool
Hot tub

Water's Edge Resort & Spa
1525 Boston Post Road, Westbrook, CT
Free cancellation
Reserve now, pay when you stay
25.1 km from city centre
The price is CA $263 per night
CA $263
CA $328 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
On private beach
Pool

Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway, Montauk, NY
29.68 km from city centre
The price is CA $552 per night
CA $552
CA $754 total
includes taxes & fees
26 Mar - 27 Mar
Stay at this 4-star beach resort in Montauk. Enjoy an outdoor pool, a full-service spa, and 2 restaurants. Our guests praise the room service in our reviews. Popular attractions Hither Woods Preserve and Hither Hills State Park are located nearby.
On private beach
Pool

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd, Old Saybrook, CT
Free cancellation
Reserve now, pay when you stay
24.93 km from city centre
The price is CA $99 per night
CA $99
CA $114 total
includes taxes & fees
25 Mar - 26 Mar
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Pet-friendly
Parking included

Hyatt Place Long Island East End
451 East Main Street, Riverhead, NY
Free cancellation
Reserve now, pay when you stay
31.4 km from city centre
The price is CA $182 per night
CA $182
CA $208 total
includes taxes & fees
1 Apr - 2 Apr
Stay at this 3-star business-friendly hotel in Riverhead. Enjoy free WiFi, free parking, and a marina. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Suffolk Theater and All Star Bowling are located nearby.
Pool
Pet-friendly

Quality Inn Old Saybrook - Westbrook
100 Essex Rd, Old Saybrook, CT
Free cancellation
Reserve now, pay when you stay
27.92 km from city centre
The price is CA $110 per night
CA $110
CA $126 total
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Old Saybrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ferry Landing State Park and Essex Saybrook Antique Village Shopping Center are located nearby.
Pool
Breakfast included

Baron's Cove
31 West Water Street, Sag Harbor, NY
8.14 km from city centre
The price is CA $280 per night
CA $280
CA $352 total
includes taxes & fees
25 Mar - 26 Mar
Stay at this 4-star hotel in Sag Harbor. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions The Hamptons Beaches and BookHampton are located nearby.
Pool
Spa

Montauk Yacht Club
32 Star Island Rd, Montauk, NY
33.98 km from city centre
The price is CA $310 per night
CA $310
CA $354 total
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Montauk Point and Montauk Marine Basin are located nearby.
On private beach
Pool

Saybrook Point Resort & Marina
2 Bridge St, Old Saybrook, CT
Free cancellation
Reserve now, pay when you stay
23.94 km from city centre
The price is CA $386 per night
CA $386
CA $473 total
includes taxes & fees
7 Apr - 8 Apr
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions General William Hart House and Katharine Hepburn Cultural Arts Center are located nearby.
Pool
Hot tub
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.
Top hotels in Shelter Island for Extended Stay

Montauk Manor
236 Edgemere St., Montauk, NY
The price is CA $188 per night from Mar. 25 to Mar. 26
CA $188
CA $243 total
includes taxes & fees
25 Mar - 26 Mar
9/10 Wonderful! (1,141 reviews)
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.
Shelter Island hotels essential information
Accommodation | 4,686 hotels |
---|---|
Lowest Price | CA $99 |
Highest Price | CA $552 |
Popular hotels | Montauk Manor, Water's Edge Resort & Spa, Gurney's Montauk Resort & Seawater Spa, Pier Blue Inn Old Saybrook - Essex, Hyatt Place Long Island East End, Quality Inn Old Saybrook - Westbrook, Baron's Cove, Montauk Yacht Club, Saybrook Point Resort & Marina |
Frequently asked questions
Recent Shelter Island hotel reviews by fellow wanderers

Saybrook Point Resort & Marina
5 out of 5
Posted 15 hours ago
Travelocity Verified Review
"We love the saybrook inn. My husband and I spent this weekend together and will be back soon
"
A verified traveller stayed at Saybrook Point Resort & Marina
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