A wooden gazebo by a pond with a large tree trunk nearby.

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov
No exact matches found, but these alternatives could be just right

Recommended hotels in Shelter Island

An outdoor seating area with umbrellas and wooden furniture, overlooking a body of water.

1. Huge Island Getaway Pool Hot Tub Walk To Beach

Huge Island Getaway Pool Hot Tub Walk To Beach
Menantic Creek
9.8 out of 10, Exceptional, (9 reviews)
"Property great. Beautiful home with great amenities"
United States
Harry K.
Huge Island Getaway Pool Hot Tub Walk To Beach
A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

2. Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful property. Everything so clean and welcoming. Slept so great in the comfortable beds. Pool is awesome. Everyone especially loved the outdoor shower"
United States
Kathleen Andrews K.
Work and Play Special! Extended Stay Discount
An outdoor patio area with string lights, tables, chairs, and a fire pit.

3. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (64 reviews)
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"
United States
Kristin
The price is AU$246
includes taxes & fees
1 Nov - 2 Nov
The Chequit
Front of property – evening/night

4. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (66 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is AU$331
includes taxes & fees
13 Oct - 14 Oct
Shelter Island House
A two-story house with a balcony, outdoor seating area, and a variety of plants.

5. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (417 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is AU$278
includes taxes & fees
13 Oct - 14 Oct
Zey Hotel
Outdoor spa tub

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (172 reviews)
"This is a great place that brings you back to a special time. Staff were exceptionally friendly and helpful. Made us feel like we were family - highly recommend."
United States
Keith
The price is AU$482
includes taxes & fees
26 Oct - 27 Oct
Silver Sands Motel & Beach Bungalows
A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

7. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (344 reviews)
"Loved everything about our stay!"
United States
Melissa
The price is AU$369
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

8. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (661 reviews)
"Great location"
United States
Jordan
The price is AU$296
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A spacious room with wicker furniture, large windows, and a view of the sea.

9. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (740 reviews)
"Great one night stay."
United States
Irene
The price is AU$357
includes taxes & fees
2 Nov - 3 Nov
Sound View Greenport
A modern house with a deck, outdoor seating, and a fire pit.

10. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (62 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is AU$409
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

11. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is AU$470
includes taxes & fees
8 Oct - 9 Oct
American Beech Hotel
Terrace/patio

12. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (295 reviews)
"Great place!"
United States
Christine
The price is AU$439
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

13. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (191 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is AU$627
includes taxes & fees
1 Nov - 2 Nov
The Menhaden
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

14. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (47 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is AU$363
includes taxes & fees
1 Nov - 2 Nov
Aqua Vista
A beach with people relaxing, a pier extending into the water, and a clear sky.

15. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (32 reviews)
"We had a great stay!! "
United States
Callie E.
The price is AU$549
includes taxes & fees
1 Nov - 2 Nov
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

16. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (52 reviews)
"Very wonderful location so close to the train station will come back soon"
United States
Julian V.
The price is AU$368
includes taxes & fees
2 Nov - 3 Nov
The SandPiper
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

17. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (291 reviews)
"Clean, great amenities, and friendly staff!"
United States
Elizabeth
The price is AU$473
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
A sign for Pier Blue Guesthouse with a logo and name.

18. 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, (1,002 reviews)
"It was a decent stay, we came in for a family reunion and originally planning to camp but weren’t able to due to the storm so we found this last min at a decent price point. Staff was very friendly when we came in, seems to be family operated which I like. Room was clean could use some updates but I liked the almost beachy vibe they have."
United States
virginia
The price is AU$129
includes taxes & fees
8 Oct - 9 Oct
Pier Blue Inn Old Saybrook - Essex
An outdoor seating area with wicker furniture, a fire feature, and glasses of red wine.

19. American Beech in Greenport - King Suite 3

American Beech in Greenport - King Suite 3
Greenport
The price is AU$453
includes taxes & fees
4 Oct - 5 Oct
American Beech in Greenport - King Suite 3
A waterfront property with a large house, multiple boats docked, and lush greenery.

20. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (671 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is AU$361
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
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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Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Nice place !"
Donald 1-night trip
Posted 8 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Shelter Island

Shelter Island Country House information

Number of reviews
3,150
Accommodation
2 Country House
Lowest Price
AU$129
Highest Price
AU$627