The Best Hotels Closest to Osprey's Dominion in Southold for 2026

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Our top choices for Osprey's Dominion hotels

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.

1. The Bentley Hotel Southampton

16.8 km from Osprey's Dominion

Frank

₩193,009

₩220,513 total

includes taxes & fees

Oct 18 - Oct 19

A waterfront property with a large house, multiple boats docked, and lush greenery.

A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.

A hotel lobby with a sofa, chairs, tables, and a large window.

A spacious hallway with a fireplace, a large window, and a built-in shelving unit.

2. Sag Harbor Inn

13.4 km from Osprey's Dominion

Terri

₩293,534

₩335,363 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

A beach with sand and sparse vegetation.

3. The Hampton Maid

18.3 km from Osprey's Dominion

SABINA

₩283,482

₩323,877 total

includes taxes & fees

Oct 13 - Oct 14

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 reception desk with a vase of flowers, a sign that says "STAY awhile", and a window with blinds.

4. Shorewood Inn

15.9 km from Osprey's Dominion

KAREN

₩114,599

₩130,924 total

includes taxes & fees

Oct 28 - Oct 29

A beachside lounge with wicker furniture, a fire pit, and string lights.

A room with a large window overlooking a body of water, featuring two wicker chairs and a table.

A spacious room with a large bed, a round table, and a wicker chair.

A beach with thatched umbrellas and a wooden walkway leading to the water.

5. Aqua by American Beech - Adults Only

17.5 km from Osprey's Dominion

Monique

₩276,244

₩362,522 total

includes taxes & fees

Oct 12 - Oct 13

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 beach scene with a sunset, calm sea, and a few people fishing.

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.

6. Hamlet Inn

17.8 km from Osprey's Dominion

Thomas

₩179,941

₩232,563 total

includes taxes & fees

Oct 4 - Oct 5

An outdoor dining area with a table and chairs, surrounded by tall trees and string lights.

A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.

A bathtub surrounded by candles and flower petals.

A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

7. A Room At The Beach

17.6 km from Osprey's Dominion

"I absolutely loved my stay at **A Room at the Beach** in Bridgehampton. Every detail of the property feels thoughtfully designed, creating an atmosphere that is both elegant and incredibly relaxing. The rooms are stylish, comfortable, and well appointed. They strike the perfect balance between luxury and warmth. What really sets this property apart, though, are the charming grounds. They've created gathering spaces that invite you to pause, read, enjoy a morning coffee, and take in the...

Barbara

₩396,875

₩453,424 total

includes taxes & fees

Oct 5 - Oct 6

A bedroom with a bed, bedside table, lamp, and a view of the outdoors through a window.

A living room area with a sofa, a dining table, and a separate queen bedroom.

A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.

A covered patio area with outdoor seating, a potted plant, and a well-maintained lawn.

8. Southampton Long Island Hotel

16.8 km from Osprey's Dominion

William

₩213,114

₩254,155 total

includes taxes & fees

Oct 4 - Oct 5

A staircase with a white railing, a white chandelier, and framed artwork on the walls.

A dining area with tables set for guests, a fireplace, and large colorful paintings on the walls.

A covered outdoor seating area with white canopies and brown furniture.

Two wine bottles with labels on a counter.

9. Harpoon House

18.2 km from Osprey's Dominion

Yuliya V

₩326,708

₩373,263 total

includes taxes & fees

Oct 14 - Oct 15

A pool area with umbrellas, potted plants, and a pathway leading to a building.

A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.

A spacious living room with a fireplace, comfortable seating, and large windows.

10. Faraway Sag Harbor

13.6 km from Osprey's Dominion

Miguel

₩548,870

₩689,800 total

includes taxes & fees

Nov 2 - Nov 3

An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.

A house with a dark blue exterior, a white porch railing, and a red door.

A window with a view of a building and trees, a small table with a lamp, and a curtain partially covering the window.

Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.

11. Ocean View Terrace Inn

18.3 km from Osprey's Dominion

Timothy

₩162,637

₩261,715 total

includes taxes & fees

Oct 22 - Oct 23

A well-maintained garden with a central pathway leading to a house.

A banquet hall with round tables set for dining, each with candles, glassware, and floral centerpieces.

A snow-covered pathway leading to a building with a porch.

12. Southampton Inn

18.4 km from Osprey's Dominion

Kevin

₩268,068

₩328,102 total

includes taxes & fees

Nov 1 - Nov 2

13. Cliffside Resort Condominiums

8.1 km from Osprey's Dominion

Christine

₩229,822

₩413,415 total

includes taxes & fees

Nov 1 - Nov 2

A building with a wooden exterior and a small porch, surrounded by a well-maintained lawn and a hedge.

A person standing on a beach, looking at a smartphone.

An outdoor dining area with a table and chairs under a tent, surrounded by a chain-link fence and a street in the background.

A well-maintained lawn in front of a building with a brick facade, multiple windows, and outdoor seating.

14. Sea Haven Resort Motel

16.9 km from Osprey's Dominion

Urvashi

₩156,014

₩199,636 total

includes taxes & fees

Nov 2 - Nov 3

A spacious room with wicker furniture, large windows, and a view of the sea.

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

A beach bar with wooden chairs and a small table, overlooking the sea.

A coastal building with large windows, a deck, and a view of the sea at sunset.

15. Sound View Greenport

7.2 km from Osprey's Dominion

Irene

₩256,984

₩331,885 total

includes taxes & fees

Nov 2 - Nov 3

A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.

A leather armchair, a small round table with a book, and a bookshelf with books and decorative items.

16. The Harbor Front Inn

9.7 km from Osprey's Dominion

Jordan

₩215,929

₩284,980 total

includes taxes & fees

Nov 2 - Nov 3

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

A hotel room with a bed, bedside tables, a desk with a chair, and a window with a view of greenery.

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

17. The Atlantic Hotel

16.6 km from Osprey's Dominion

Chris

₩119,625

₩170,182 total

includes taxes & fees

Oct 28 - Oct 29

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

A spacious room with wooden flooring, a bar area with stools, and large windows allowing natural light.

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

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

18. Hampton Bays Hotel on Main

19.5 km from Osprey's Dominion

desirae

₩158,146

₩180,682 total

includes taxes & fees

Oct 6 - Oct 7

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Compare popular hotels close to Osprey's Dominion

Property	Property class	Guest rating
The Bentley Hotel Southampton	9.6 Exceptional 593 reviews	View
Sag Harbor Inn	9.4 Exceptional 671 reviews	View
The Hampton Maid	9.2 Wonderful 793 reviews	View
Shorewood Inn	8.4 Very good 823 reviews	View
Aqua by American Beech - Adults Only	9.2 Wonderful 361 reviews	View

Top Osprey's Dominion Hotel Reviews

Zey Hotel

10/10 Excellent

"Lots of space to sit and talk or work or catch up with friends. Only minor thing for me personally was no decaf coffee because it meant that my mom waited for me to run to get some. Great location for walking everywhere and not taking the car. And the only reason we haven’t booked every year before is we didn’t know it was there. Will be back again."

The Shoals Suites and Slips

10/10 Excellent

"The staff were all great, the food from food truck was delicious, check in was quick!"

Vine & Sand

10/10 Excellent

"The hosts were very friendly and welcoming. They were always available when we had questions or needed anything. We enjoyed the fresh pastries and fresh fruit the 1st morning. They were very accommodating and had breakfast out early when we had to leave extra early for our event our 1st day."

Other attractions near Osprey's Dominion

Pindar Vineyards

8.4/10 (8 reviews)

You can enjoy a tasting or tour at Pindar Vineyards during your travels to Peconic. Discover the area's sunsets and wineries.

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Corey Creek Winery

9.6/10 (5 reviews)

You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

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Mattebella Vineyards

8.0/10 (4 reviews)

You can enjoy a tasting or tour at Mattebella Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

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Croteaux Vineyards

10.0/10 (12 reviews)

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

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Raphael Winery

You can enjoy a tasting or tour at Raphael Winery during your travels to Peconic. Wander the beaches or discover the area's sunsets.

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Custer Institute and Observatory

Enjoy an outing to Custer Institute and Observatory during your stay in Southold. Wander the beaches and gardens while you're in the area.

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Lenz Winery

10.0/10 (3 reviews)

You can enjoy a tasting or tour at Lenz Winery during your travels to Peconic. Discover the area's sunsets and wineries.

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Frequently asked questions

What's the area like around Osprey's Dominion?

Osprey's Dominion is located in a family-friendly area of Southold known for its beautiful beaches. If you're looking for a convenient place to stay, check out the 25 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Osprey's Dominion?

Vine & Sand is one of the top choices for your stay based on our traveler data, and this B&B offers free breakfast and free parking. It's located just a short 0.6 mi (0.9 km) from Osprey's Dominion.

How many hotels are there close to Osprey's Dominion?

Expedia has 25 hotels and other accommodations within a mile from Osprey's Dominion.

If I need to cancel the hotel reservation for my stay near Osprey's Dominion, will I receive a refund?

Yes! The majority of hotel room reservations are fully refundable if you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your scheduled arrival. If you have a reservation that's non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to view the best options available near Osprey's Dominion.

Where can I learn more about changing or cancelling my trip in the area near Osprey's Dominion?

To access more information about picking new dates or cancelling your stay near Osprey's Dominion, click here.

What can I see and do near Osprey's Dominion?

Get outside and spend some time strolling around Goldsmith's Inlet Park, Horton Point Park, and Cutchogue Village Green. Crescent Beach, Sunset Beach, and Horton Lane Beach are great spots if you want to spend some time by the water during your stay. Create some family memories at Custer Institute and Observatory and 8 Hands Farm.

Find hotels near Osprey's Dominion, Southold from ₩130,924

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Our top choices for Osprey's Dominion hotels

1. The Bentley Hotel Southampton

2. Sag Harbor Inn

3. The Hampton Maid

4. Shorewood Inn

5. Aqua by American Beech - Adults Only

6. Hamlet Inn

7. A Room At The Beach

8. Southampton Long Island Hotel

9. Harpoon House

10. Faraway Sag Harbor

11. Ocean View Terrace Inn

12. Southampton Inn

13. Cliffside Resort Condominiums

14. Sea Haven Resort Motel

15. Sound View Greenport

16. The Harbor Front Inn

17. The Atlantic Hotel

18. Hampton Bays Hotel on Main

Compare popular hotels close to Osprey's Dominion

Top Osprey's Dominion Hotel Reviews

Zey Hotel

The Shoals Suites and Slips

Vine & Sand

Other attractions near Osprey's Dominion

Pindar Vineyards

Corey Creek Winery

Sannino's Bella Vita Vineyard

Mattebella Vineyards

Croteaux Vineyards

Raphael Winery

Custer Institute and Observatory

Lenz Winery

Frequently asked questions