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Find Hotels in Town of Southold Town, NY

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***NEW HOT TUB AWAITS YOU***
The price is $350 per night from Nov 30 to Dec 1
8.75 mi from city center
4.9/5Exceptional! (36 reviews)
great weekend getaway spot

"My friends and I had a lovely weekend here. The location was great and close to all the vinyards. The house was very comfortable and we would stay again!"…"

Reviewed on Nov 17, 2020

***NEW HOT TUB AWAITS YOU***
Remodeled Greenport Apartment By Greenport Harbor
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1.99 mi from city center
5/5Exceptional! (27 reviews)
Great place in Greenport

"Very close to water. 5 min walk to town of Greenport. ~1 mile bike ride to ferry to Shelter Island. Great location! The street has a lot of charm and the inside of this property is very clean and well appointed just as advertised. Spent 4 nights here and would love to come back!"…"

Reviewed on Aug 15, 2020

Remodeled Greenport Apartment By Greenport Harbor
Orient Point Cottage With Private Beach
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5.23 mi from city center
4.8/5Exceptional! (5 reviews)
Quiet Stay

"Great experience very pleasant owners house is in a lovely neighborhood, Beautiful pool close to town the bay and the sound very peaceful stay would return again."…"

Reviewed on Oct 1, 2019

Orient Point Cottage With Private Beach
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Quaint Cottage Close to LI Sound
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8.18 mi from city center
4.9/5Exceptional! (30 reviews)
Perfect getaway

"The space was extremely clean and well equipped. The perfect space for two people."…"

Reviewed on Nov 17, 2020

Quaint Cottage Close to LI Sound
Cottage Getaway, Family Friendly W/ Saltwater Heated Pool - Close To Everything
5/5Exceptional! (2 reviews)
Beautiful property & Amazing location

"Perfect summer getaway with a beautiful outdoor pool. Each room has its own bathroom. House is well maintained and the property is located close to farms, restaurants, beaches and vineyards. Highly recommended with families traveling with children."…"

Reviewed on Aug 19, 2020

Cottage Getaway, Family Friendly W/ Saltwater Heated Pool - Close To Everything
Classic 1812 Farmhouse w/ Heated Gunite Pool-sweeping Farm Views; Open air
4.5/5Wonderful! (15 reviews)
Perfect getaway

"Aaron was the most gracious host, texting to stay in communication as needed (recommendations upfront, check out info at the end) but never ever overbearing. The week was just what we wanted — a relaxing getaway in the middle of beautiful farms and vineyards with a stunning deck and backyard to help ..."…"

Reviewed on Oct 27, 2020

Classic 1812 Farmhouse w/ Heated Gunite Pool-sweeping Farm Views; Open air
The Lane House North Fork Private Beach Escape
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5.46 mi from city center
4.7/5Exceptional! (3 reviews)
Wonderful memories

"Wonderful and quite neighborhood, house fully equipped, spacious and clean. Our children loved to play in the garden and our dinners were nicely served on the backyard terrace. In addition to the private beach (walking distance), you are only few minutes away (driving) from the Orient Point County ..."…"

Reviewed on Sep 18, 2020

The Lane House North Fork Private Beach Escape
Walk to Train and Town
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5.88 mi from city center
Walk to Train and Town
New Home....walk to the Beach....fun in the Sun!
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4.3 mi from city center
5/5Exceptional! (5 reviews)
Loved this property

"The house was gorgeous and the owners were very accommodating. Ocean views and everything that you could possibly need was provided. I strongly recommend this property."…"

Reviewed on Oct 14, 2019

New Home....walk to the Beach....fun in the Sun!
Newly Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants
4.4/5Wonderful! (22 reviews)
Perfect Stay

"Great clean property in excellent location. Walkable to town. easy entry and parking. Would highly reccomend."…"

Reviewed on Oct 22, 2020

Newly Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants
American Beech Hotel
3.5 out of 5
300 Main Street, Greenport, NY
The price is $136 per night from Dec 8 to Dec 9
2.13 mi from city center
4.4/5Excellent! (89 reviews)

"Excellent location, clean rooms, beautiful decor. Can’t wait to stay again!"…"

Reviewed on Mar 17, 2020

American Beech Hotel
The Gallery Hotel
3.5 out of 5
439 Main Street, Greenport, NY
The price is $149 per night from Nov 25 to Nov 26
2.1 mi from city center
4.6/5Wonderful! (134 reviews)

"The hotel is conveniently located, and has very cool decor throughout. It's decorated with a mid-century modern touch. Nice contemporary artworks, too. The courtyard/lounge area in the back is beautiful and very inviting. I would stay there again, without hesitation. My stay happened to coincide ..."…"

Reviewed on Oct 30, 2020

The Gallery Hotel
Southold Beach Motel
2 out of 5
53250 North Road, Southold, NY
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4.73 mi from city center
4.1/5Very Good! (90 reviews)

"The room and bathroom were sparkling clean. This small motel was probably built in the 1950’s so it’s dated , but for us it was perfect. The lady running the office was charming , friendly, and helpful. The room had a small kitchenette with a small microwave and 2 stovetop burners. It also had a ..."…"

Reviewed on Oct 30, 2020

Southold Beach Motel
Stirling House Bed & Breakfast
3 out of 5
104 Bay Avenue, Greenport, NY
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2.03 mi from city center
4.9/5Exceptional! (8 reviews)

"Great property and wonderful host. I would go there again."…"

Reviewed on Aug 20, 2019

Stirling House Bed & Breakfast
Quintessentials Bed & Breakfast & Spa
4 out of 5
8985 Main Road, East Marion, NY
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0.48 mi from city center
4.7/5Exceptional! (3 reviews)
Relaxing trip

"Let me just say this was my first time at a bnb and i was nervous about it but now i cant wait to go back. The inn keeper Sylvia was so pleasant and the breakfast was great. The rooms have there own bathroom and the best word to describe it would be quaint."…"

Reviewed on Sep 14, 2018

Quintessentials Bed & Breakfast & Spa
Shorecrest Bed and Breakfast
3.5 out of 5
54300 County Route 48, Southold, NY
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4.53 mi from city center
4.8/5Exceptional! (13 reviews)

"BEautiful place, with friendly and accomodating inn keeper, with extremely clean and comfortable accomodations."…"

Reviewed on Jul 23, 2019

Shorecrest Bed and Breakfast
North Fork Guest House
3.5 out of 5
35995 Main Road, Cutchogue, NY
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9.7 mi from city center
4.9/5Exceptional! (10 reviews)

"This is a lovely inn with even lovelier hosts! Absolutely exceeded my expectations."…"

Reviewed on Nov 27, 2019

North Fork Guest House
Orient Inn
4 out of 5
25500 Main Road, Orient, NY
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2.86 mi from city center
4.9/5Exceptional! (22 reviews)

"The inn is a beautiful Arts and Crafts style house. It was very comfortable and inviting. We were very pleased with our accommodations. The breakfasts served were fantastic."…"

Reviewed on Sep 25, 2018

Orient Inn
Shinn Estate Vineyards and Farmhouse
4 out of 5
2000 Oregon Road, Mattituck, NY
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12.7 mi from city center
4.7/5Exceptional! (18 reviews)
30th Birthday Getaway Over Winter Break

"My husband & I spent two days at the Shinn Estate Winery over our winter break while celebrating my 30th birthday. The rooms are beautiful and the breakfast and evening cheese plate & wine made our trip! Keep in mind, the beds are Queen sized. My husband is over 6 feet tall and just barely fit! This ..."…"

Reviewed on Dec 30, 2017

Shinn Estate Vineyards and Farmhouse
Cliffside Resort Condominiums
3 out of 5
61475 Route 48 (North Road), Greenport, NY
The price is $230 per night from Nov 29 to Nov 30
3.18 mi from city center
4.4/5Excellent! (103 reviews)
A must stay!

"Exceeded my expectations! Highly recommend. Room was beautiful, small private beach with lounge chairs provided. 5 minute car ride to town! But honestly you never need to even leave this place. The sunsets are beautiful!"…"

Reviewed on Jul 27, 2020

Cliffside Resort Condominiums
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Town of Southold Town Hotel Guide

Expedia.com offers a selection of 321 hotels in Town of Southold Town. You are sure to find cheap deals and discount rates among them with our Best Price Guarantee. No matter what type of hotel strikes your fancy, we will let you search for your preferred one to accommodate your travel needs.

Expedia.com will not only save you time, but also money when booking your stay at a hotel in Town of Southold Town. Making reservations so you can stay within your budget is easy with us.

Expedia.com even provides you with a map so you may find cheap hotels in the Town of Southold Town neighborhood you prefer.

Go ahead. Enter your travel dates to view the best offers on hotel rooms in Town of Southold Town, New York now, including last minute deals!

Frequently asked questions

Where is the best place to stay in Town of Southold Town?
The Menhaden is a favorite property for Expedia customers. This 3.5-star hotel offers 2 bars and free breakfast. Traveler reviews also recommend The Harborfront Inn and The Gallery Hotel as top choices for your trip.
If I need to cancel my hotel reservation in Town of Southold Town, will I receive a refund?
Yes, most room reservations are refundable provided that you cancel prior to the hotel’s cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and be given a refund within a 24-hour period of booking. Plug in your dates, click on “Search”, then you can use the “free cancellation” filter to review the best deals available in Town of Southold Town.
Where can I learn more about changing or cancelling my trip to Town of Southold Town?
To access more information about updating your trip to Town of Southold Town or cancelling it, go to https://www.expedia.com/service/.
What's the best hotel for a romantic vacation in Town of Southold Town?
Arbor View House Bed and Breakfast is a favorite 3.5-star B&B for couples, and features Frette Italian sheets and 2 spa tubs. Other good options for your romantic getaway include Quintessentials Bed & Breakfast & Spa and Stirling House Bed & Breakfast.
What's the best pet-friendly accommodation in Town of Southold Town?
The Blue Inn At North Fork is a top inn for people traveling with their pets, and offers a seasonal outdoor pool and a bar/lounge for its human guests.
What's the best accommodation for a beach vacation in Town of Southold Town?
Sound View Greenport is a top 3-star beachfront hotel with a seasonal outdoor pool and free breakfast, and it’s located close to 67 Steps Beach. Other good choices for your beach trip include Southold Beach Motel and Cliffside Resort Condominiums.
What's the best luxury place to stay in Town of Southold Town?
Arbor View House Bed and Breakfast is a luxury B&B with spa services and 2 outdoor tennis courts, and it’s a popular choice for Expedia travelers looking for an elegant place to stay.
What's the best boutique hotel in Town of Southold Town?
The Gallery Hotel is a favorite 3.5-star hotel with our travelers looking for a stylish accommodation, featuring 10 guestrooms, a restaurant, and a bar.
What's the best place to stay if I'm looking to play golf in Town of Southold Town?
Arbor View House Bed and Breakfast is a top 3.5-star B&B that has a golf driving range and features free breakfast. Another good option is Quintessentials Bed & Breakfast & Spa if you’d like to stay near a golf course while in town. You can tee off at Island’s End Golf and Country Club during your trip.
What are some hotels with pools in Town of Southold Town?
The Blue Inn At North Fork is a top inn with a seasonal outdoor pool, free WiFi, and free parking. Other choices that offer an onsite pool include Heron Suites and Cliffside Resort Condominiums.

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