Holiday Rentals in Town of Southold Town

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Town of Southold Town holiday rentals

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is €238
includes taxes & fees
20 May - 21 May
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is €235
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €275
includes taxes & fees
21 May - 22 May
American Beech in Greenport - Petite King Room 7

Northfork Townhouse walk to all

Northfork Townhouse walk to all
Greenport
10.0 out of 10, Exceptional, (5 reviews)
"Great property located in a quiet neighborhood within walking distance to all in Greenport. The townhouse was clean and kitchen was well- appointed with off the street parking. Playground up the street was an added bonus with a old school merry-go-round! Would definitely stay again"
United States
Beth R.
The price is €582
includes taxes & fees
18 May - 19 May
Northfork Townhouse walk to all

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1 review)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is €841
includes taxes & fees
19 May - 20 May
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

New Construction Greenport Pool House - 3 Blocks from Town

New Construction Greenport Pool House - 3 Blocks from Town
Greenport
10.0 out of 10, Exceptional, (3 reviews)
"This was a great house for a large group! It was clean, and the backyard was perfect for our group to enjoy. The host was quick to respond to any questions we had. "
United States
Alexis P.
The price is €1,096
includes taxes & fees
27 May - 28 May
New Construction Greenport Pool House - 3 Blocks from Town

American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1 review)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is €319
includes taxes & fees
18 May - 19 May
American Beech in Greenport - Deluxe King 6

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is €281
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,346 reviews)
"Had a wonderful stay"
United States
Meghan
The price is €165
includes taxes & fees
21 May - 22 May
Montauk Manor

The Tiny Cottage on The Pond

The Tiny Cottage on The Pond
Oakdale,
10.0 out of 10, Exceptional, (8 reviews)
"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"
United States
Sharon O.
The price is €165
includes taxes & fees
25 May - 26 May
The Tiny Cottage on The Pond

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (42 reviews)
"We had such a wonderful one night stay at Shalom Cottage! The place was absolutely beautiful—so cozy, clean, and thoughtfully decorated. Raj, the host was truly amazing! He was kind, responsive, and made sure we had everything we needed from start to finish. We felt so welcomed and comfortable the entire time. We would definitely love to stay here again and highly recommend it to anyone! "
United States
Alexis F.
The price is €193
includes taxes & fees
19 May - 20 May
1-bedroom cottage with Grove Beach 🏖️ access.

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (178 reviews)
"A bright and cozy vibe as well as being thoroughly equipped with everything to make our stay comfortable.We appreciated the winter escape and enjoyed Stonington, Mystic, and Westerly. A lovely stay!"
United States
Dawn R.
The price is €217
includes taxes & fees
19 May - 20 May
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is €196
includes taxes & fees
21 May - 22 May
Windward Shores Ocean Resort

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (238 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is €181
includes taxes & fees
19 May - 20 May
Driftwood Resort

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Old Mystic
10.0 out of 10, Exceptional, (21 reviews)
"Host was very responsive and the room was really nice clean. Would definitely stay there again!"
United States
Pamela O.
The price is €190
includes taxes & fees
20 May - 21 May
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (8 reviews)
"A beautiful place to stay! Comfortable, cozy and clean. All amenities and the surprise dessert was awesome! We will definitely be back!"
United States
Tammy Z.
The price is €166
includes taxes & fees
18 May - 19 May
A Mystic Stay as Sweet as Apple Pie!

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Norwich
9.8 out of 10, Exceptional, (51 reviews)
"Great location"
United States
Jeff F.
The price is €204
includes taxes & fees
26 May - 27 May
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Norwich
10.0 out of 10, Exceptional, (42 reviews)
"My girlfriend and I had a wonderful time here it was GREAT.!"
United States
Kareem
The price is €278
includes taxes & fees
18 May - 19 May
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (36 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is €208
includes taxes & fees
20 May - 21 May
Walk To Goodspeed Opera House!

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (33 reviews)
"Host went out their way to make it special for my husband's 70th Birthday! This was our second time staying here. Very clean and accommodating to our needs."
United States
Lori R.
The price is €265
includes taxes & fees
18 May - 19 May
Peaceful Oasis Steps from Mohegan Sun
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Town of Southold Town Hotel Reviews

Find out more about Town of Southold Town

Holiday Homes in Town of Southold Town

Search for holiday homes in Town of Southold Town on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Town of Southold Town using one of the methods below: 

  • View our selection of featured holiday homes in Town of Southold Town
  • Use the map to find apartments and other holiday rentals in the Town of Southold Town neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Town of Southold Town while they last

Look no further and take a look at our great range of rental properties in Town of Southold Town!