2 Stars Hotels in Shelter Island: Compare Hotel Prices & Find the Cheapest Shelter Island, New York 2 Stars Hotels

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Our top choices for Shelter Island 2-star hotels

Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.

A guesthouse named Pier Blue with a sign, a parking lot, and a building with a red awning.

A train traveling along a river with autumn foliage in the background.

1. Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

Egor

NT$2,644

NT$3,040 total

includes taxes & fees

Aug 27 - Aug 28

A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.

A kitchen counter with a coffee maker, thermos, fruits, and breakfast items.

2. The Atlantic Hotel

Southampton

Jessa

NT$6,283

NT$7,976 total

includes taxes & fees

Sep 8 - Sep 9

A modern hotel lobby with a seating area, a reception desk, and a view of the street.

A spacious lawn with a dining area and a building with a covered patio.

A bedroom with a bed, bench, lamp, and artwork on the wall.

A modern kitchen with a dark island, a dining area with a sofa and chair, and a view of the outdoors.

3. Budget Host East End

Riverhead

Natalya

NT$3,984

NT$4,552 total

includes taxes & fees

Aug 27 - Aug 28

A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

A modern living room with a flat-screen TV, a dining area with a round table and chairs, a sofa with cushions, and a small side table with a lamp.

A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

4. The Bentley Hotel Southampton

Southampton

Frank

NT$5,387

NT$6,951 total

includes taxes & fees

Sep 7 - Sep 8

A garden with a wooden bench, a playground, and a house in the background.

A stone fireplace with a built-in bench, a window with a view of trees, and a stone floor.

A swimming pool with a child on a pink and white inflatable float.

A hotel room with two beds, a desk, a coffee maker, and a view of greenery through the window.

5. Hampton's Vacation Inn

Hampton Bays

Brian

NT$6,456

NT$7,376 total

includes taxes & fees

Aug 31 - Sep 1

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

A hotel room with a large bed, a bathroom with a bathtub, a TV on a wooden cabinet, and a chair.

A dining area with tables and chairs, a clock on the wall, and a counter with food items.

6. Quality Inn Old Saybrook - Westbrook

Old Saybrook

Theresa

NT$3,224

NT$3,708 total

includes taxes & fees

Sep 20 - Sep 21

A hotel room with a bed, a desk with a TV, a small table, and chairs. There is a balcony with a view of the ocean.

An indoor swimming pool with two separate sections, surrounded by lounge chairs and a covered area with large windows.

A hotel room with a bed, a desk, a chair, a TV, and a view of the ocean.

A beach with rows of blue umbrellas and beach chairs.

7. Montauk Blue Hotel

Downtown Montauk

Maria

NT$5,203

NT$7,504 total

includes taxes & fees

Sep 7 - Sep 8

An outdoor swimming pool area with lounge chairs and a covered seating area.

A spacious living room with a dark wooden coffee table, a grey sofa, and a patterned rug.

A bedroom with a bed, bedside tables, a dresser, a ceiling fan, and a framed picture on the wall.

A building with a sign reading "FARMERS MARKET".

8. Kenny's Tipperary Inn

Culloden Shores

Tiara

NT$4,706

NT$5,591 total

includes taxes & fees

Sep 15 - Sep 16

A hotel room with a sofa, a coffee table, a TV, and a framed picture on the wall.

A kitchen with a sink, a coffee maker, a vase with flowers, and a framed picture on the wall.

A room with a round table, two white chairs, a potted plant, and a window with curtains.

A living room with a sofa, a wooden cabinet, a television, and a framed picture on the wall.

9. Hotel Corduroy

Culloden Shores

jiayu

NT$11,582

NT$14,423 total

includes taxes & fees

Sep 8 - Sep 9

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

A modern living room with a stone wall, a flat-screen TV mounted above a door, a dark sofa, and a glass coffee table with a vase of flowers.

A beach with sand and sparse vegetation.

A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.

10. The Hampton Maid

Hampton Bays

Adam

NT$8,319

NT$9,504 total

includes taxes & fees

Sep 8 - Sep 9

A wooden beach boardwalk leading to the ocean.

A wooden beach gate with signs, a sandy path, and a clear blue sky.

A modern building with a pool area, including a pool, lounge chairs, and a covered area with a water feature.

A covered outdoor seating area with wooden chairs and tables, potted plants, and hanging flower baskets.

11. Aqualina Inn Montauk

Downtown Montauk

Matthew

NT$6,215

NT$7,101 total

includes taxes & fees

Sep 21 - Sep 22

A beachside walkway leading to a wooden gazebo with benches and tables, overlooking a body of water.

An outdoor bar area with a canopy, tables, and a bartender.

A bedroom with a large window, a bed, a lamp, and a view of a body of water.

A building with a gabled roof, large windows, and a door with a number.

12. Barlume Beach Montauk

Montauk

Alexa

NT$9,610

NT$12,077 total

includes taxes & fees

Sep 10 - Sep 11

A bedroom with a bed, a nightstand, a lamp, artwork on the wall, and a window with curtains.

13. Sea Crest Resort

Amagansett

Liliana

NT$8,670

NT$10,599 total

includes taxes & fees

Sep 8 - Sep 9

A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

A bedroom with a bed, a door, and a framed picture on the wall.

A white closet with shelves, a robe hanging on a wooden hanger, and a pair of black straps on a rack.

A breakfast bar with cereal, coffee, and fresh milk.

14. Shorewood Inn

Riverhead

KAREN

NT$5,766

NT$6,588 total

includes taxes & fees

Aug 27 - Aug 28

A covered outdoor area with a wooden staircase, green chairs, and hanging flower baskets.

A round mirror with a woven frame reflecting a room with a bed, pillows, a small table, and a window with curtains.

A poolside area with sun loungers, a large umbrella, and a house in the background.

15. Ocean Resort Inn

Downtown Montauk

Jennifer

NT$6,215

NT$7,101 total

includes taxes & fees

Sep 21 - Sep 22

A wooden deck with green cushioned chairs overlooking the ocean.

A pool area with lounge chairs and a pool, overlooking a beach with a wooden fence and beachgoers.

A wooden deck with lounge chairs facing the ocean.

16. Ocean Surf Resort

Downtown Montauk

Jeffrey

NT$5,068

NT$7,176 total

includes taxes & fees

Sep 21 - Sep 22

A modern hotel room with a large bed, a framed picture on the wall, and a wooden floor.

A spacious bar area with a long counter and multiple stools, a brick wall with a mural, and exposed pipes on the ceiling.

A compact kitchen with white cabinetry, a built-in dishwasher, and a coffee maker on the countertop.

A two-story building with a sign reading "Squiretown Rd" and a storefront with a sign that says "B&B."

17. Hampton Bays Hotel on Main

Hampton Bays

Deborah

NT$4,219

NT$4,821 total

includes taxes & fees

Sep 14 - Sep 15

A garden with a fountain, various shrubs, and flower beds.

A motel with a two-story structure, a covered parking area, and a landscaped front yard with various plants.

A kitchen with wooden cabinets, a refrigerator, a coffee maker, and a fruit bowl.

A reception area with a wooden counter, a bulletin board with various notices, a potted plant, and a door leading to another room.

18. Liberty Inn

Old Saybrook

William

NT$2,840

NT$3,266 total

includes taxes & fees

Sep 10 - Sep 11

Two people standing on a deck with a view of a lake and greenery.

A spacious room with a large sliding glass door leading to an outdoor deck with a pool and umbrellas.

A spacious dining area with large windows offering a view of the outdoors. There are multiple tables and chairs arranged for dining.

A sign for Bayview Resort with a contact number.

19. Bayview Resort

Hampton Bays

Darryl

NT$6,498

NT$7,424 total

includes taxes & fees

Sep 13 - Sep 14

20. Sun N Sound

Culloden Shores

Gina

NT$8,301

NT$10,004 total

includes taxes & fees

Sep 3 - Sep 4

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Explore similar 3-star hotels

Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Shelter Island.

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

NT$11,761

NT$14,641 total

Sep 3 - Sep 4

includes taxes & fees

9.6/10 Exceptional! (1,013 reviews)

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

NT$7,430

NT$9,094 total

Sep 14 - Sep 15

includes taxes & fees

Zey Hotel

439 Main Street Greenport NY

NT$6,454

NT$7,374 total

Aug 30 - Aug 31

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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.

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

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

Top Shelter Island Hotel Reviews

Ocean Resort Inn

10/10 Excellent

"Great spot to stay! Location was ideal and staff was amazing"

The Bentley Hotel Southampton

8/10 Good

"nice room for the price in season"

Montauk Blue Hotel

10/10 Excellent

"Great place to stay!! Walking distance to town. Love it!!"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Absolute gem really cool giant picnic table in the middle of the room, which is great for kids are just getting work done. The staff is absolutely wonderful. The view is gorgeous. If you stay on the backside of the hotel cannot recommend this place enough. What a surprise incredible bargain."

Budget Host East End

8/10 Good

"We came for the pool and enjoyed every minute of a few relaxing days poolside. Lush green grounds provided some shady picnic tables when it was time to get out of the sun. If you are looking for an inexpensive stay not far from the Hamptons or North Fork this is your place. Staff, especially, front desk, very nice, friendly and informative. Rooms had a mini fridge and comfy bed. A/C worked great. Try to get a poolside room. Hotel includes continental breakfast on weekends. Multiple excellent restaurant options nearby on Main Street. We would recommend Olga's for breakfast, offers outdoor/indoor seating. For dinner there is Cliff's Rendezvous steak house. Call and go when they offer their steak special night. Jerry and the Mermaid for seafood, also has outdoor/indoor seating by the water. There is Tweed's where you can try Buffalo. And a few hidden gems with great water views and outdoor seating -Turkuaz (Turkish food ) and Country Farm Kitchen. There is Atlantis Aquarium nearby, that also offers boat tours of the Peconic by day and booze cruises weekend eves. Suffolk Theatre offers well known artists in concert on the weekends. There are at least 4 breweries a short drive away and homemade ice cream at Snowflake and homemade chocolate at North Fork Chocolate & Eatery. Polish Town is nearby if you want Polish food try the Birchwood Restaurant or groceries from the town's deli's."

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Book 2 Star Hotels in Shelter Island on Expedia.com

Shelter Island 2 Stars Hotels

Change your mind

Treat yourself

Be picky

Check availability on Shelter Island 2 Star Hotels

Our top choices for Shelter Island 2-star hotels

1. Pier Blue Inn Old Saybrook - Essex

2. The Atlantic Hotel

3. Budget Host East End

4. The Bentley Hotel Southampton

5. Hampton's Vacation Inn

6. Quality Inn Old Saybrook - Westbrook

7. Montauk Blue Hotel

8. Kenny's Tipperary Inn

9. Hotel Corduroy

10. The Hampton Maid

11. Aqualina Inn Montauk

12. Barlume Beach Montauk

13. Sea Crest Resort

14. Shorewood Inn

15. Ocean Resort Inn

16. Ocean Surf Resort

17. Hampton Bays Hotel on Main

18. Liberty Inn

19. Bayview Resort

20. Sun N Sound

Explore similar 3-star hotels

Saybrook Point Resort & Marina

Water's Edge Resort & Spa

Zey Hotel

Learn more about Shelter Island

Top Shelter Island Hotel Reviews

Ocean Resort Inn

The Bentley Hotel Southampton

Montauk Blue Hotel

Pier Blue Inn Old Saybrook - Essex

Budget Host East End

Explore a world of travel with Expedia