A calm lake with a forest in the background during sunset.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Southold

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (346 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is CA $262
CA $335 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
A spacious room with wicker furniture, large windows, and a view of the sea.

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (758 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is CA $253
CA $330 total
includes taxes & fees
Nov 16 - Nov 17
Sound View Greenport
A lakeside patio with outdoor seating and a view of the water.

3. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (178 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 CA $325
CA $371 total
includes taxes & fees
Nov 2 - Nov 3
Silver Sands Motel & Beach Bungalows
An outdoor patio area with string lights, tables, chairs, and a fire pit.

4. The Chequit

The Chequit
3.0 star property
The Heights
9.2 out of 10, Wonderful, (69 reviews)
"Friendly staff , Unique property."
United States
Patrick
The price is CA $210
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
The Chequit
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, (431 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is CA $237
CA $271 total
includes taxes & fees
Oct 27 - Oct 28
Zey Hotel
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.

6. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (667 reviews)
"Great hotel with friendly staff, clean and comfortable rooms, and excellent service — I really enjoyed my stay!"
United States
Antrii
The price is CA $253
CA $330 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
Terrace/patio

7. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is CA $239
CA $430 total
includes taxes & fees
Nov 12 - Nov 13
Cliffside Resort Condominiums
A serene landscape with a calm body of water reflecting trees with autumn foliage.

8. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is CA $261
CA $299 total
includes taxes & fees
Nov 2 - Nov 3
House on Chase Creek
Front of property - evening/night

9. 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 CA $285
CA $325 total
includes taxes & fees
Oct 19 - Oct 20
Shelter Island House
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

10. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (300 reviews)
"incredible stay, pet friendly and very accommodating. Staff was so kind!"
United States
Allison
The price is CA $296
CA $373 total
includes taxes & fees
Nov 18 - Nov 19
Oyster Estate
A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (66 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is CA $414
CA $473 total
includes taxes & fees
Oct 19 - Oct 20
North Fork Resort
A waterfront property with a large house, multiple boats docked, and lush greenery.

12. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (680 reviews)
"Free parking, clean, continental breakfast good quality."
United States
Terri
The price is CA $310
CA $354 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A pathway flanked by lush greenery and bamboo, leading to a building with a wooden exterior.

13. 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 CA $355
CA $462 total
includes taxes & fees
Oct 19 - Oct 20
American Beech Hotel
A round table with a magazine, a plate with a pastry, a cup, and a vase with flowers.

14. Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (838 reviews)
"Beautiful hotel vintage"
United States
Dennis
The price is CA $145
CA $166 total
includes taxes & fees
Oct 19 - Oct 20
Shorewood Inn
A modern building entrance with a black and white striped awning, a staircase leading inside, and two bicycles parked outside.

15. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (192 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is CA $489
CA $615 total
includes taxes & fees
Nov 16 - Nov 17
The Menhaden
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, (57 reviews)
"Place was perfect ! Great location / clean/ everything we needed was there ! Would love to stay there again :)"
United States
Manuela C.
The price is CA $134
CA $355 total
includes taxes & fees
Nov 10 - Nov 11
The SandPiper
A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

17. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (50 reviews)
"Great location and nice spot."
United States
Kerri L.
The price is CA $134
CA $355 total
includes taxes & fees
Nov 9 - Nov 10
Aqua Vista
A beach with people relaxing on chairs and sunbathing.

18. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is CA $134
CA $360 total
includes taxes & fees
Nov 2 - Nov 3
Harbor Heights
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

19. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (600 reviews)
"WOW What a nice hotel. Perfect location for Hampton Bays & Southampton. Very clean, very modern & very nice"
United States
Doug
The price is CA $191
CA $218 total
includes taxes & fees
Oct 31 - Nov 1
The Bentley Hotel Southampton
A beach with people relaxing, a pier extending into the water, and a clear sky.

20. 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, (34 reviews)
"We had a wonderful stay in Greenport! The location was absolutely perfect, and one of the things we loved most was being able to walk to town and the beautiful harbor. Everything was so conveniently located, from the charming shops and wonderful restaurants to the lovely waterfront, making it easy to enjoy everything Greenport has to offer without needing to drive. We would happily stay here again and highly recommend this place to anyone looking for a wonderful Greenport getaway!"
United States
Nino
The price is CA $205
CA $544 total
includes taxes & fees
Nov 2 - Nov 3
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
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 Southold 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 8 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold Residences information

Number of reviews
4,189
Accommodation
1 Residences
Lowest Price
CA $166
Highest Price
CA $615

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