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Reviews
Reviewed 4 weeks ago
Shelter Island Escape

We stayed at the Ram's Head Inn and greatly enjoyed our experience. The rooms are nice, but the real draw is the location and property grounds. The beautiful lawn rolls down to a private beach. The... more

Reviewed 4 November 2017
Got Married October 2012

My wife and I got married there in 2012, all of our guests loved every minute of it. The owners and staff were awesome. We had every room at the Inn, the food we requested was the best. If the... more

Contact
108 Ram Island Drive, Shelter Island, NY 11965
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Beachfront
  • Restaurant
  • Bar/Lounge
No availability for your dates from these sites
#2 Best Value of 5 hotels in Shelter Island
Reviews
Reviewed 3 September 2017
A Love Hate Hotel

Ok - we arrive by train from Penn Station - a long journey. We arrive to catch the Ferry over to Shelter Island. Luckily met the nicest family on the ferry and they asked where we were staying... more

Reviewed 23 August 2017
Disappointed- last year we will be here

We have been coming to Shelter Island for 38 years. Many of the last several years have been spent here at Sunset Beach Hotel. The property, hotel and management have gone down exponentially. This... more

Contact
35 Shore Rd, Shelter Island, NY 11965-2002
Amenities
  • Free Wifi
  • Free Parking
  • Beachfront
  • Restaurant
  • Room Service
  • Bar/Lounge
No availability for your dates from these sites
#3 Best Value of 5 hotels in Shelter Island
Reviews
Reviewed 20 October 2017
Amazing place to stay!

We stayed at the Shelter Island House for a family wedding a couple of weeks ago and couldn't have been more pleased with our stay. The accommodations were just lovely, our room was clean and... more

Reviewed 27 July 2017
Girls Weekend Getaway

This place was much better than expected. I booked without ever visiting Shelter Island and reading a few negative reviews and went with my gut based on positive reviews and pictures and was right... more

Contact
11 Stearns Point Rd, Shelter Island, NY 11965-2009
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Restaurant
  • Bar/Lounge
Hotels near Shelter Island (25)
Booking.com
USD 133*
View Deal
7.1 km from Shelter Island
Savings alert! 19% below average rates

The price you found is 19% lower than this hotel's average rate of USD 164/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 26 October 2017
A Hidden Gem in the North Fork!

We had a delightful sat for 2 nights back in September. Just perfect for a quick getaway. The décor was quaint, the room was clean. This was off a main road but the lodging is way n the back. No... more

Reviewed 25 September 2017
Lovely room/Uncomfortable mattress

Large spacious room. Very clean. Includes a kitchenette with cooking utensils , cutlery, dishes and glasses. Very adequate room amenities. Close to Greenport. Very reasonably priced. The reason it... more

Contact
7850 Main Rd, East Marion, NY 11939-1505
(631) 449-7535
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
SAVE USD 70
USD 222*
Groupon.com
USD 152*
View Deal
7.2 km from Shelter Island
Savings alert! 15% below average rates

The price you found is 15% lower than this hotel's average rate of USD 179/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 6 days ago
Cozy Winter Get Away

Great overnight get away, especially for a groupon deal. Very cozy in the winter. Great fireplace in the tavern / lobby. Rooms are nicely decorated in a nautical type theme. Little outdoor patio... more

Reviewed 26 December 2017
Sisters weekend

Had a groupon and although still pricey it was very nice. I had a waterfront room (213?) which had a gorgeous view of the bridge and water, a king size bed and a loft with a nice size living area. We... more

Contact
31 West Water St., Sag Harbor, NY 11963
+1 844-227-6672
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Restaurant
  • Room Service
  • Bar/Lounge
SAVE USD 16
USD 553*
Travelocity
USD 537*
View Deal
14.0 km from Shelter Island
Savings alert! 13% below average rates

The price you found is 13% lower than this hotel's average rate of USD 618/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 12 January 2018
New Year’s Eve Party

So much fun! Awesome party! Great food, great drinks, great music, great atmosphere. The small hors d'oeuvre were delicious!!!! Highly recommend coming here! If you want a great party thats not... more

Reviewed 27 November 2017
Hamptons with style

I booked this hotel in a very last minute and was positively surprised that it even has a Jean Georges restaurant. Our room was on the second floor, and it was very spacious and stylishly decorates... more

Contact
1 Bridgehampton - Sag Harbor Turnpike, Bridgehampton, NY 11932
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Restaurant
  • Room Service
Booking.com
USD 179*
View Deal
20.6 km from Shelter Island
Reviews
Reviewed 17 November 2017
Off Season Getaway

Stayed here in November. The receptionist was very helpful in explaining whats around, food suggestions and things we could do with the dog. The Inn is well kept and we were in a corner King room. It... more

Reviewed 15 October 2017
Good witha few porblems

Its very close to the town so you can walk in for a meal or a wander around. We were on the first floor, which involved lugging cases up stairs, which seemed quite steep or maybe I'm getting older... more

Contact
91 Hill St, Southampton, NY 11968-5399
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Restaurant
  • Bar/Lounge
Expedia.com
USD 100*
View Deal
21.5 km from Shelter Island
Reviews
Reviewed 8 August 2017
An outrageously priced motel

I had to stay there for one night with family to avoid driving 40 minutes back from an event in SH - the "deluxe studio" was a dump and none of us, kids or adults, could get any sleep as the beds are... more

Reviewed 23 July 2017
not what i expected

for a hotel that is over $ 400 /night, when I pulled up I thought it looked like a motel 6. yes it is in the hamptons, but on the very busy stretch of highway. Breakfast is included but is was a... more

Contact
1655 County Road 39, Southampton, NY 11968-5254
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
Travelocity
USD 268*
View Deal
Reviews
Reviewed 1 week ago
The place to go to feel special

My daughters treated me to an overnight stay at this beautiful inn. If you like being made to feel special, this is the place to go. Having stayed stayed here last May (my youngest daughter chose SPI... more

Reviewed 2 weeks ago
Very comfortable stay

This place was hopping for January, but w figured it was mostly New Yorkers or New Englanders looking for a relaxing spa weekend. We thought the price for the room at this time of year was very high... more

Contact
2 Bridge St, Old Saybrook, CT 06475-2566
(860) 390-2156
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Restaurant
  • Room Service
  • Bar/Lounge
Travelocity
USD 118*
View Deal
25.6 km from Shelter Island
Reviews
Reviewed 6 days ago
Lanak9

Loved the place. It was quaint & very clean. The owner was very hospitable. Great location to visit wineries & farm stands. I went to a Women’s Christian Event in Mattituck & Duncan Inn was the... more

Reviewed 4 weeks ago
Super clean, super cute!

I was in Mattituck for celebration of a loved one's life. I was fortunate enough to stay at the Duncan Inn. It was lovely, very clean and modern. The rooms are small, but so comfortable! If you... more

Contact
1399 Main Rd, West, Jamesport, NY 11947
Amenities
  • Free Wifi
  • Free Parking
SAVE USD 2
USD 68*
Travelocity
USD 66*
View Deal
Reviews
Reviewed 22 November 2017
good value..great owner

The rooms were clean. The furniture was handmade and really unique. There was a set of table and chairs so we were able to play cards at night. Ajay could not have been nicer. He would do... more

Reviewed 28 October 2017
Nice place to stay for a reasonable price

I stayed at Pier Blue on Sept 23 and had booked a month before at a very reasonable price. My stay was a very pleasant one. The motel had a large room, which had been painted recently and new beds... more

Contact
1430 Boston Post Rd, Old Saybrook, CT 06475-1709
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
SAVE USD 5
USD 67*
EconoLodge
USD 62*
View Deal
Reviews
Reviewed 14 October 2017
One night stay enroute to Maine

Was an ok stay for one night but I wouldn't stay there for any length of time. Room was "standard" size and reasonably clean. Spots and stains on bedspread but I always remove those anyway. Good... more

Reviewed 3 September 2017
Emphasis is on economy

Our standard two queen room was very small. The chair didn't fit with the desk and you couldn't sit in it without it backing up right into the bed. The windows don't open so you are reliant on the ac... more

Contact
1750 Boston Post Rd, Old Saybrook, CT 06475-1642
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Fitness centre
Booking.com
USD 68*
View Deal
28.1 km from Shelter Island
Special offer
Special OfferBOOK ON OUR WEBSITE
Reviews
Reviewed 11 November 2017
Fine place to stay in Old Saybrook

Everything was fine. The Manager was very pleasant. The highway sound did not bother us. We believe we smelled cigarette smoke during the night. Perhaps our next door neighbor. We would stay her... more

Reviewed 27 September 2017
All that we needed

We got the room with 2 queen beds .It was fine very reasonably priced. Breakfast was just enough to get you going.Quiet ,thou close to 95. Room was clean. Wonderful friendly family run. Very close to... more

Contact
55 Springbrook Rd, Old Saybrook, CT 06475-1225
(860) 387-7656
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
Booking.com
USD 126*
View Deal
32.0 km from Shelter Island
Savings alert! 11% below average rates

The price you found is 11% lower than this hotel's average rate of USD 141/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 3 weeks ago
Perfect location

I had my engagement party at the Long Island Aquarium this past weekend and stayed at this hotel which is conveniently right next door. All of my guests are still raving over the amazing staff and... more

Reviewed 3 weeks ago
Great gooms in a great location

Stayed here overnight while I attended a party at the Aquarium (which is right next door!) and it was great. The rooms were SO spacious. It is close to a few great restaurants and bars, and being... more

Contact
451 E Main St, Riverhead, NY 11901-2556
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Restaurant
  • Room Service
SAVE USD 20
USD 109*
Booking.com
USD 89*
View Deal
32.1 km from Shelter Island
Special offer
Special OfferPay 2 Nights 1 Free
Savings alert! 12% below average rates

The price you found is 12% lower than this hotel's average rate of USD 101/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 20 November 2017
James & Jennifer

We LOVED this place!!! Definitely decidedly not fancy but a great homey feel almost like a b&b! Clean and cozy and won't kill your bank account!!! Perfectly situated between the beach & down... more

Reviewed 16 November 2017
Cute Little Montauk Motel

Great location. I like that they kept the 70s style motif of the property (it is updated). Staff was super friendly. I went in the off season so the price was great. Room had a kitchen and a patio... more

Contact
44 S Elmwood Ave, P.O. Box 687, Montauk, NY 11954-5374
(631) 657-2219
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
SAVE USD 18
USD 138*
Expedia.com
USD 120*
View Deal
Reviews
Reviewed 1 week ago
Great overall experience!

My boyfriend and I booked a last minute trip to Montauk and decided to stay at Kenny’s Tipperary Inn. It was great! We arrived around 1 AM and they were still up waiting for us. We asked if we could... more

Reviewed 2 weeks ago
Away for anniversary

It was nice and quiet good place if you looking to rejuvenate peaceful. Can use some updating though wasn't totally please with the room. Didn't feel comfortable using the tub had cracks in the... more

Contact
432 W Lake Dr, P.O. Box 5015, Montauk, NY 11954-5126
(631) 214-2043
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Restaurant
SAVE USD 55
USD 144*
Booking.com
USD 89*
View Deal
32.9 km from Shelter Island
Savings alert! 15% below average rates

The price you found is 15% lower than this hotel's average rate of USD 105/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 27 November 2017
clean and freshly painted

The room was clean and looked of fresh paint. This is a very older motel with little updates. Signage is dull and not light when we arrived. Front desk was polite, but seemed preoccupied. This is for... more

Reviewed 20 August 2017
Not bad

It was clean, reasonably priced and near where I needed to go. It wasn't the greatest place as far as amenities but got the job done. It does need updating, but wasn't unpleasant. Although, the... more

Contact
30 Lake Ave, Riverhead, NY 11901-3502
Amenities
  • Free Wifi
  • Free Parking
  • Pool
SAVE USD 12
USD 229*
Booking.com
USD 217*
View Deal
33.2 km from Shelter Island
Special offer
Savings alert! 15% below average rates

The price you found is 15% lower than this hotel's average rate of USD 255/night.

We analyze rates over a 60 day period, and compare your selection to the average rate of comparable stays to ensure you're getting the best possible deal.

Reviews
Reviewed 1 week ago
Madison Beach Hotel

We have stayed at the Madison Beach Hotel many times. It is our little get away from home - but close to home. We love it. From the fireplace in the room, to the view, to the spa facilities and... more

Reviewed 2 weeks ago
Great Getaway Weekend!

This was the perfect place for a winter getaway. Even in the middle of winter, the beach is a wonderful place. Love the heated outdoor patio dining. The room was beautiful and extremely clean... more

Contact
94 W Wharf Rd, Madison, CT 06443-2905
+1 855-605-0316
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Beachfront
  • Restaurant
  • Room Service
  • Bar/Lounge
SAVE USD 8
USD 80*
Booking.com
USD 72*
View Deal
34.4 km from Shelter Island
Special offer
Reviews
Reviewed 21 August 2017
really bad

the room was just nasty after you get looking around it.There was mold all around I did't sit my bag on the carpert because it was so nasty an was afiend that my bag would catch some thing. the... more

Reviewed 17 August 2017
Last-minute and better value for families.

My family first asked to see a room before booking because of the reviews and what we saw was better than expected. The motel's dated and may have several long-term renters but the staff were... more

Contact
265 Flanders Rd, Niantic, CT 06357-1214
(860) 850-0891
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
Hotels.com
USD 64*
View Deal
Reviews
Reviewed 5 September 2017
Not bad....basically okay

Stayed one night in August 2017. The room was kinda small for me and 3 kids. I asked for non-smoking but I'm quite sure that at one point in time in the past it was a smoking room. It's very hard to... more

Reviewed 9 August 2017
Fishing trip

We stayed at Motel 6 for a quick overnight trip from NY to CT. The front desk was accommodating. The room was clean, new floors and very spacious. The only thing that should be changed or fixed is... more

Contact
269 Flanders Rd, Niantic, CT 06357-1213
Amenities
  • Free Parking
TripAdvisor
View Deal
Reviews
Reviewed 5 October 2017
More ideal on a non-wedding weekend

We were here the same weekend that a wedding was being held on the property. I think this lends itself to a very different experience than what we could have had on any other weekend. The grounds are... more

Reviewed 25 August 2017
Nice surprise

Boutique little resort...has a European and hippy feel! Modest accommodations but very clean. The landscaping is beautiful. Meals and drinks available on site were good. Entertainment one night... more

Contact
90 Second House Rd, Montauk, NY 11954-5063
(631) 668-2105
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Restaurant
  • Bar/Lounge
Hotels.com
View Deal
Reviews
Reviewed 21 October 2017
Excellent value in expensive Montauk

This place is a gem and hopefully will stay that way. The prices were excellent and probably will not be beat in Montauk for what is a lovely stay. Very nice staff at check in, lovely relaxed pool... more

Reviewed 5 October 2017
Cute Scandinavian Style Motel

The owners did a great job updating and brightening up an otherwise drab motel. The paint, new beds, furniture and fixtures were all tastefully chosen. We checked in after the office had already... more

Contact
533 W Lake Dr, Montauk, NY 11954-5152
(631) 668-7000
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Beachfront
SAVE USD 13
USD 124*
Expedia.com
USD 111*
View Deal
35.1 km from Shelter Island
Special offer
Reviews
Reviewed 3 weeks ago
Aqsa

I was helped by Aqsa at the Riverhead, New York location and I was highly satisfied. The computers were down but she made sure my information got into the system before her shift was over. She was... more

Reviewed 9 November 2017
Very very nice.

Had to book a hotel room, unrelated travel nightmare. Ended up at this venue in the wee hours, completely exhausted. Very highly recommend this hotel - extremely gracious and helpful night manager... more

Contact
1707 Old Country Rd, Riverhead, NY 11901-4422
011 61 1800 760 595
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Fitness centre
Booking.com
USD 78*
View Deal
35.5 km from Shelter Island
Reviews
Reviewed 20 August 2017
Weekend visit

My husband and I needed a place to stay for a family wedding in Southampton on Aug. 19. The prices of hotels in the area at this time of year (or maybe, at all times) were exorbitant. After looking... more

Reviewed 4 June 2017
HOMELESS SHELTER/NOT A MOTEL

We booked a room here for an overnight stay while going to the raceway. It was booked through another booking site, with recent good reviews The front of the establishment looked well kept, but it... more

Contact
1433 W Main St, Riverhead, NY 11901-3111
Amenities
  • Free Parking
Travelocity
USD 132*
View Deal
36.3 km from Shelter Island
Special offer
Reviews
Reviewed 1 week ago
Fantastic hotel

Stayed here with my wife and daughter. Can’t speak more highly of the quality of service and gorgeous rooms. First class all around. Will stay here again. Check in was fast and greeted with a smile... more

Reviewed 3 weeks ago
Great hotel; Great staff

After dealing with complacency from the HGI next door I decided to check in to this brand new hotel and I was pleasantly surprised at the difference in service levels. Rinaldo, Patrick, Jessica, the... more

Contact
2012 Old Country Rd, Riverhead, NY 11901-3149
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Fitness centre
Expedia.com
USD 55*
View Deal
Reviews
Reviewed 26 October 2017
Friendly staff, very clean and quiet.

We chose this hotel because they had smoking rooms and were near our destination. The front desk gentleman was very friendly and helpful. The hotel itself could use some upgrading and the breakfast... more

Reviewed 22 August 2017
A very enjoyable stay

We spent 4 nights here last week. We had a lovely time, made special by Booker, the receptionist who was most helpful at all times. From the breakfast chat to sorting out our GPS with a phone call... more

Contact
211 Waterford Pkwy N, Waterford, CT 06385-1209
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Fitness centre
SAVE USD 12
USD 133*
HotelIndigo.com
USD 121*
View Deal
Reviews
Reviewed 19 December 2017
Convenient location, excellent value

The Hotel Indigo is located on the outskirts of Riverhead, on West main street, just off of NY State Rte 25. Therefore, it is easy access from Manhattan, Queens, and all communities on the East End... more

Reviewed 19 October 2017
The Hamptons and shopping too !

Had a great dinner and stay at Indigo, shopped at the Tanger Mall stores, got some bargains and spend a lot of money. If you can handle spending some money, you will appreciate the nice things you... more

Contact
1830 W Main St, Route 25, Riverhead, NY 11901-3113
011 61 1800 760 595
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Restaurant
  • Room Service
  • Bar/Lounge
Priceline
USD 55*
View Deal
Reviews
Reviewed 7 December 2017
Mohegan Sun Alternative

Great alternative to casino Hotel Cost effective way if you are just going to play and don’t want to drop triple the price for convenience Budget minded hotel clean and what you would expect from a... more

Reviewed 25 October 2017
great place

nice place. well mannered and friendly staff. satisfied with the service there. no complaints. feel like home. vinie, the staff member treated as good as expected. all the comfort provided. will... more

Contact
707 Colman St, I-95 at Frontage Road, Exit 82-A/83, New London, CT 06320-2605
Amenities
  • Free Wifi
  • Free Parking
Other hotels you may like
Reviews
Reviewed 10 October 2017
Serene Shelter Island

This was our first time visiting Shelter Island , celebrating our son's wedding. The Dering Harbor Inn has an excellent location overlooking the harbor. Each accommodation, whether it be a studio... more

Reviewed 27 August 2017
fun

Beautiful hotel the rooms are hugIe. Very clean great service, great gym and best location. I wouldn't stay anywhere else. Studio was exceptionally large. Barbara is the best. The food is great... more

Contact
13 Winthrop Road, Shelter Island, NY 11965
Amenities
  • Free Wifi
  • Free Parking
  • Pool
  • Fitness centre
No availability for your dates from these sites
Reviews
Reviewed 14 September 2017
Great location but rooms need upgrade

The location is right on the water and the atmosphere is transfixing, but the hotel is old and the rooms need an upgrade. That said, our stay was very nice and in fact the hotel is aware of it's... more

Reviewed 20 July 2017
Family of 4 in a large room

We had tagged The Pridwin stay onto a 5 night Manhattan stay. Such a welcome rest and contrast. Lovely relaxed feel, very clean with a very nice and deep pool, direct access to a beach area and... more

Contact
81 Shore Road, Crescent Beach, Shelter Island, NY 11964
(631) 489-8596
Hotel website
Amenities
  • Free Wifi
  • Free Parking
  • Breakfast included
  • Pool
  • Beachfront
  • Restaurant