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Shelter Island 2 Stars Hotels

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Check availability on Shelter Island 2 Star Hotels

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Shelter Island 2-star hotels

A sign for Pier Blue Guesthouse with a logo and name.
Two blue Adirondack chairs and a small white table in a grassy area surrounded by trees.
A train traveling along a river with autumn foliage in the background.
A hotel room with two beds, a wooden bench, a desk, a mirror, and a patterned carpet.

1. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Celina
NT$2,295
NT$2,639 total
includes taxes & fees
Oct 19 - Oct 20
Pier Blue Inn Old Saybrook - Essex
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 hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.
A sign for 'The Atlantic Southampton' with a stylized logo and text.

2. The Atlantic Hotel

The Atlantic Hotel
Southampton
United States
miranda
NT$3,470
NT$4,775 total
includes taxes & fees
Oct 28 - Oct 29
The Atlantic Hotel
A modern hotel lobby with a seating area, a reception desk, and a view of the street.
A modern kitchen with a dark island, a dining area with a sofa and chair, and a view of the outdoors.
A swimming pool with a diving board, surrounded by a fenced patio area with benches and a small building.
A bedroom with a bed, bench, lamp, and artwork on the wall.

3. Budget Host East End

Budget Host East End
Riverhead
United States
Lannie
NT$2,884
NT$3,295 total
includes taxes & fees
Oct 19 - Oct 20
Budget Host East End
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

4. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Doug
NT$4,374
NT$4,997 total
includes taxes & fees
Oct 31 - Nov 1
The Bentley Hotel Southampton
A wooden deck with green cushioned chairs overlooking the ocean.
A beachfront property with a multi-level structure, including a balcony and a staircase leading to the beach.
A wooden deck with lounge chairs facing the ocean.
A pool area with lounge chairs and a pool, overlooking a beach with a wooden fence and beachgoers.

5. Ocean Surf Resort

Ocean Surf Resort
Downtown Montauk
United States
DAWN
NT$3,532
NT$5,444 total
includes taxes & fees
Oct 19 - Oct 20
Ocean Surf Resort
A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.
A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.
A bedroom with a large bed, a chandelier, and multiple windows.
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.

6. The Hampton Maid

The Hampton Maid
Hampton Bays
United States
Joshua
NT$6,853
NT$7,829 total
includes taxes & fees
Oct 26 - Oct 27
The Hampton Maid
An outdoor swimming pool area with lounge chairs and a covered seating area.
A well-maintained hedge in front of a building with a white facade and black window frames.
A building with a sign reading "FARMERS MARKET".
A spacious living room with a dark wooden coffee table, a grey sofa, and a patterned rug.

7. Kenny's Tipperary Inn

Kenny's Tipperary Inn
Culloden Shores
United States
Jaysen
NT$3,483
NT$4,138 total
includes taxes & fees
Oct 22 - Oct 23
Kenny's Tipperary Inn
An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.
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.
A living room with two sofas, a coffee table, a lamp, and a painting on the wall.

8. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Amy
NT$3,140
NT$3,611 total
includes taxes & fees
Nov 8 - Nov 9
Quality Inn Old Saybrook - Westbrook
Beach
Living area
Exterior
Sundeck

9. Sun N Sound

Sun N Sound
Culloden Shores
United States
MARSILDA
NT$4,208
NT$5,336 total
includes taxes & fees
Nov 1 - Nov 2
Sun N Sound
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 hotel room with two beds, a desk, a coffee maker, and a view of greenery through the window.
A dining area with wicker chairs, a glass table, and a flat-screen TV mounted on the wall.

10. Hampton's Vacation Inn

Hampton's Vacation Inn
Hampton Bays
United States
Christopher
NT$7,728
NT$8,829 total
includes taxes & fees
Oct 19 - Oct 20
Hampton's Vacation Inn
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.
A reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.
A bedroom with a bed, a door, and a framed picture on the wall.
A breakfast bar with cereal, coffee, and fresh milk.

11. Shorewood Inn

Shorewood Inn
Riverhead
United States
Dennis
NT$3,324
NT$3,798 total
includes taxes & fees
Oct 19 - Oct 20
Shorewood Inn
Terrace/patio
Private kitchen
A bedroom with a bed, a nightstand, a lamp, artwork on the wall, and a window with curtains.
Exterior

12. Sea Crest Resort

Sea Crest Resort
Amagansett
United States
Dan
NT$6,380
NT$7,995 total
includes taxes & fees
Oct 19 - Oct 20
Sea Crest Resort
A sandy beach with footprints leading to the water, a grassy dune on the left, and a cloudy sky.
A sign for Ocean Vista with a red and white van parked nearby.
A large indoor swimming pool with multiple lanes, safety signs, and a tiled wall with hexagonal patterns.
A coastal pathway with a wooden bridge leading to a green sports court.

13. Ocean Vista Resort

Ocean Vista Resort
Amagansett
United States
Dan
NT$4,682
NT$5,349 total
includes taxes & fees
Oct 19 - Oct 20
Ocean Vista Resort
A blue door, a small table with a potted plant, and a green chair on a porch.
A bedroom with two wicker chairs, a TV, and two wardrobes.
A compact kitchen with a sink, a coffee machine, and a window overlooking a natural landscape.
A small, single-story house with a blue door and multiple windows.

14. Marina Bay Cottages

Marina Bay Cottages
Waterford
United States
Tara
Marina Bay Cottages
A modern hotel room with a large bed, a framed picture on the wall, and a wooden floor.
A two-story building with a sign reading "Squiretown Rd" and a storefront with a sign that says "B&B."
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.

15. Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
Hampton Bays
United States
Richard
NT$3,823
NT$4,368 total
includes taxes & fees
Oct 19 - Oct 20
Hampton Bays Hotel on Main
A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace in the background.
A spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A beach scene with a sunset, calm sea, and a few people fishing.

16. Hamlet Inn

Hamlet Inn
Southampton
United States
Eric
NT$5,158
NT$6,667 total
includes taxes & fees
Nov 16 - Nov 17
Hamlet Inn
A wooden beach boardwalk leading to the ocean.
A modern building with a pool area, including a pool, lounge chairs, and a covered area with a water feature.
A check-in area with a wooden bench, a small table, and a window with blinds.
A covered outdoor seating area with wooden chairs and tables, potted plants, and hanging flower baskets.

17. Aqualina Inn Montauk

Aqualina Inn Montauk
Downtown Montauk
United States
Michael
Aqualina Inn Montauk
Two people standing on a deck with a view of a lake and greenery.
A sign for Bayview Resort with a contact number.
A spacious dining area with large windows offering a view of the outdoors. There are multiple tables and chairs arranged for dining.
A spacious room with a large sliding glass door leading to an outdoor deck with a pool and umbrellas.

18. Bayview Resort

Bayview Resort
Hampton Bays
United States
Hanna
NT$5,055
NT$5,775 total
includes taxes & fees
Oct 19 - Oct 20
Bayview Resort
A wooden beach boardwalk leading to the ocean.
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.
A covered outdoor area with a wooden staircase, green chairs, and hanging flower baskets.

19. Ocean Resort Inn

Ocean Resort Inn
Downtown Montauk
United States
Christina
Ocean Resort Inn
A garden with a fountain, various shrubs, and flower beds.
A hotel room with a large bed, two bedside lamps, a wooden nightstand, a desk with a chair, and a view of the outdoors through a window.
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.

20. Liberty Inn

Liberty Inn
Old Saybrook
United States
Grace
NT$2,887
NT$3,320 total
includes taxes & fees
Oct 25 - Oct 26
Liberty Inn
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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.
Water's Edge Resort & Spa

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT
NT$5,781
NT$7,207 total
Nov 2 - Nov 3
includes taxes & fees
Water's Edge Resort & Spa
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
NT$4,623
NT$6,867 total
Nov 5 - Nov 6
includes taxes & fees
Montauk Blue Hotel
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT
NT$8,716
NT$11,157 total
Nov 18 - Nov 19
includes taxes & fees
Saybrook Point Resort & Marina
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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 coastal landscape with a lake, dense greenery, and a sunset sky.

Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Very clean bathroom. Very dated and weathered furniture. The linens were good. The paint on the door needed cleaned. The receptionist was very personable. We were on the first level and could hear the folks above."
kimberly 1-night trip
Posted 18 hours ago
Pier Blue Inn Old Saybrook - Essex
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."
Cynthia 7-night trip
Posted 5 days ago
The Bentley Hotel Southampton

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