Southold

Southold Homestays

Enter your dates to find homestays in Southold for a cozy, local feel.

Scroll down to see hotels
Filter by:
Hotel Star Rating
≤2345
Guest Rating
Amazing 9+Great 8+Good 7+Pleasant 6+

Popular Homestays in Southold

Check out the best homestays in Southold for a home-like stay.
Most Booked
Lowest Price
Closest to Downtown
Highest Rated
Gorgeous Historical 6 bdrm House close to vineyards and breweries,
Gorgeous Historical 6 bdrm House close to vineyards and breweries,Gorgeous Historical 6 bdrm House close to vineyards and breweries,Gorgeous Historical 6 bdrm House close to vineyards and breweries,Gorgeous Historical 6 bdrm House close to vineyards and breweries,Gorgeous Historical 6 bdrm House close to vineyards and breweries,Gorgeous Historical 6 bdrm House close to vineyards and breweries,
41
Hotels in Southold
This property is a newly renovated historical Victorian House built in the late 1800's. Each room is furnished with hand-selected unique antiques to immerse you into the 19th century. Staying here feels like experiencing the past, but with all the benefits of modern life!Excellent location for Bachellorretes, Weddings, Family gatherings. The house has plenty of space for up to 14 people to sleep comfortably and large dining tables to fit a family.Fully loaded with a pantry and full sized kitchen. A patio is available to you if you choose to do outdoor BBQ. There is grass space for your children to run around as well!This property is in the heart of the NORTHFORK wine country.The nearby locations of this area are outstanding!- You can walk to plenty of wineries and vineyards in just minutes.- The Greenport Harbor Brewery is just a 5 minute walk.- You can travel to this location with the HAMPTON JITNEY since the bus station is also just a short walk.If you have a car available to you then: - You can drive in 5 minutes to nice beaches.- You can drive to Southold & Greenport town and explore the plethora of options available to you, including playgrounds, restaurants, and stores to shop in.Come by and enjoy fishing, boating, hiking, golfing, tennis, bird watching and anything else there is to offer!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Adults only.About customRules:Owner sometimes lives in own quarters. Uses a separate discreet entrance. Will not interfere with guests..In case of small groups, not all rooms may be available. Please note , rates are for 6 people additional adults are subject to additional fees.,No Large Gatherings NO PROMS or PARTIES/EVENTS No additional guests allowed beyond what was stated in booking..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.UNLESS DISCUSSED WITH OWNER.
Outstanding
5 reviews
10.0/10
Check Availability
Greenport Walk to beach & vineyard from this brand new home
Greenport Walk to beach & vineyard from this brand new homeGreenport Walk to beach & vineyard from this brand new homeGreenport Walk to beach & vineyard from this brand new homeGreenport Walk to beach & vineyard from this brand new homeGreenport Walk to beach & vineyard from this brand new homeGreenport Walk to beach & vineyard from this brand new home
25
Hotels in Southold
Featured facilities: Clothes Dryer
Outstanding
5 reviews
10.0/10
Check Availability
Bayfront Vacation Home in Southold, 5 Bedrooms
Bayfront Vacation Home in Southold, 5 BedroomsBayfront Vacation Home in Southold, 5 BedroomsBayfront Vacation Home in Southold, 5 BedroomsBayfront Vacation Home in Southold, 5 BedroomsBayfront Vacation Home in Southold, 5 BedroomsBayfront Vacation Home in Southold, 5 Bedrooms
25
Hotels in Southold
Featured facilities: Clothes Dryer
Outstanding
4 reviews
10.0/10
Check Availability
Southold
You Might Like
Southold Hotels Including BreakfastSouthold Hotels With Twin RoomSouthold Hotels With 1 Double BedSouthold Hotels With Swimming PoolSouthold Hotels With Free Cancellation
House of Classic Arts and Crafts North Fork
House of Classic Arts and Crafts North ForkHouse of Classic Arts and Crafts North ForkHouse of Classic Arts and Crafts North ForkHouse of Classic Arts and Crafts North ForkHouse of Classic Arts and Crafts North ForkHouse of Classic Arts and Crafts North Fork
17
Hotels in Southold
This charming Southold village house sits on a half acre with a back deck overlooking a sweeping backyard. Newly furnished and freshly painted, it is centrally located to wineries, bay and sound beaches and is a short walk to shops. Enjoy the sunset on the deck or in the hammock and maybe get a glimpse of a deer family that often walk by. Come enjoy all that the wonderful North Fork has to offer! Taxes: as of 2023, Suffolk County is requiring us to charge 5.5% tax per booking, please note this is in addition to State of New York sales tax of 8.625%, hence the total taxes due are bundled together for a total of 14.125%....About pets:No pets allowed.No.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Yes.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.No.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.No.
Outstanding
5 reviews
9.8/10
Check Availability
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine CountrySteps from Cedar Beach ! Tranquil Retreat in the Heart of Wine CountrySteps from Cedar Beach ! Tranquil Retreat in the Heart of Wine CountrySteps from Cedar Beach ! Tranquil Retreat in the Heart of Wine CountrySteps from Cedar Beach ! Tranquil Retreat in the Heart of Wine CountrySteps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
30
Hotels in Southold
Featured facilities: Clothes Dryer
Amazing
4 reviews
9.6/10
Check Availability
Water Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large Deck
Water Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large DeckWater Front Beach House w/ Private Beach with 3 Bedrooms/2 Bathrooms/Large Deck
37
Hotels in Southold
Featured facilities: Kitchen, Washing Machine
Outstanding
5 reviews
9.8/10
Check Availability
Lovely Cottage in the Heart of Long Island Wine country
Lovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine countryLovely Cottage in the Heart of Long Island Wine country
21
Hotels in Southold
Featured facilities: Kitchen
Outstanding
18 reviews
9.8/10
Check Availability
“Paradise Found” - Walk to Private Beach & in-Ground Pool!
“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!“Paradise Found” - Walk to Private Beach & in-Ground Pool!
23
Hotels in Southold
Featured facilities: Kitchen, Washing Machine
Outstanding
5 reviews
10.0/10
Check Availability
Country BEACH home!
Country BEACH home!Country BEACH home!Country BEACH home!Country BEACH home!Country BEACH home!Country BEACH home!
27
Hotels in Southold
Featured facilities: Washing Machine
Outstanding
9.8/10
Check Availability
4BR NOFO Home in Heart of Wine Country (w/pool)
0
Check Availability
See all Homestays in Southold

Frequently Asked Questions

How do I book a hotel on Trip.com?

To book a hotel on Trip.com, simply enter your destination, travel dates, and the number of guests on the page. Then, browse through the available hotels and select the one you want to book. Follow the prompts to enter your payment information and complete the booking.

How do I get hotel deals on Trip.com?

There are several ways to find affordable hotels on Trip.com. You can narrow down your search results by filtering hotels according to your preferred price range, or you can sort the results by price to view the cheapest options first.

Where can I find hotel deals on Trip.com?

Trip.com offers a wide variety of hotel deals and promotions that are available throughout the year. You can easily find these special offers on our deals page. What's more, if you are a member of our loyalty program, you can sign in to your account and discover exclusive discounted rates at hotel list pages.

How can I get lower prices for hotels?

Sometimes booking hotels midweek is cheaper, but it also depends on the season.

How many hotels are listed on Trip.com?

You’ll find over 1,500,000 hotels in 230+ countries and regions on Trip.com. Can’t decide which hotel to book? Browse the site for inspiration!

Can I cancel or change my hotel bookings on Trip.com?

It depends on the hotel policy and date of cancellation. Please check the policy section of the related hotel pages. To cancel or change your bookings, sign in to your Trip.com account, go to "My Bookings", and follow the instructions.

How do I contact Trip.com customer support?

You can contact Trip.com's 24/7 customer support by visiting the Help Center on Trip.com and submitting a request. You can also contact us by phone or service chat, depending on your location.