Vacation Rentals in Town of Southold Town

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Our top choices for Town of Southold Town vacation rentals

Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is ￥30,976
￥42,309 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
The price is ￥44,670
￥51,035 total
includes taxes & fees
Jun 15 - Jun 16
North Fork Resort
Interior

Breakwater Estate… perfect for Large Group Getaways!

Breakwater Estate… perfect for Large Group Getaways!
Mattituck
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is ￥155,587
￥273,133 total
includes taxes & fees
Jun 25 - Jun 26
Breakwater Estate… perfect for Large Group Getaways!
Dining

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 ￥58,047
￥113,259 total
includes taxes & fees
Jun 1 - Jun 2
Northfork Townhouse walk to all
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
The price is ￥61,630
￥117,901 total
includes taxes & fees
May 31 - Jun 1
Renovated Townhouse walk to all
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is ￥33,283
￥50,764 total
includes taxes & fees
May 31 - Jun 1
American Beech in Greenport - Petite King Room 7
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is ￥119,676
￥199,865 total
includes taxes & fees
May 31 - Jun 1
Beachfront Greenport Villa
Smart TV, books

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 ￥111,157
￥186,675 total
includes taxes & fees
Jun 4 - Jun 5
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds

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 ￥39,653
￥59,132 total
includes taxes & fees
May 31 - Jun 1
American Beech in Greenport - Deluxe King 6
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,355 reviews)
"Had a wonderful stay"
United States
Meghan
The price is ￥58,054
￥69,447 total
includes taxes & fees
Jun 30 - Jul 1
Montauk Manor
Apartment | Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
The price is ￥30,161
￥39,647 total
includes taxes & fees
Jun 1 - Jun 2
Driftwood Resort
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (313 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 ￥54,206
￥66,261 total
includes taxes & fees
May 31 - Jun 1
Windward Shores Ocean Resort
Apartment | Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is ￥32,510
￥38,876 total
includes taxes & fees
Jun 1 - Jun 2
Montauk Oceanside Suites
Apartment | Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (281 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is ￥44,615
￥59,636 total
includes taxes & fees
Jun 1 - Jun 2
The Surf Club
Smart TV, books

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, (179 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 ￥16,086
￥41,434 total
includes taxes & fees
Jun 2 - Jun 3
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Outdoor dining

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 ￥26,120
￥49,190 total
includes taxes & fees
Jun 10 - Jun 11
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Property grounds

Lakeside cottage overhanging the water, beautiful window views across the lake

Lakeside cottage overhanging the water, beautiful window views across the lake
Ledyard
9.8 out of 10, Exceptional, (229 reviews)
"wonderful place to stay. the pond is beautiful. plenty to do nearby "
United States
Mike
The price is ￥35,035
￥63,939 total
includes taxes & fees
Jun 3 - Jun 4
Lakeside cottage overhanging the water, beautiful window views across the lake
Interior

Charming Historic House in Downtown Mystic

Charming Historic House in Downtown Mystic
Mystic
10.0 out of 10, Exceptional, (180 reviews)
"Host was very welcoming and the house was so charming. Great location "
United States
Andrea C.
The price is ￥35,115
￥66,022 total
includes taxes & fees
May 31 - Jun 1
Charming Historic House in Downtown Mystic
Property grounds

Lakeside cottage ON the water with beautiful views up the lake!

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (199 reviews)
"We had a wonderful stay at the cottage! It was so cozy and peaceful, exactly what we were looking for. Mini splits kept our rooms toasty on the cold night, and we had everything we needed. Our host was super communicative and helpful. Would definitely stay here again!"
United States
Anonymous traveler
The price is ￥37,583
￥69,178 total
includes taxes & fees
Jun 2 - Jun 3
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (56 reviews)
"Stayed here for Valentine's weekend with my wife and it was perfect! Gardner and Kathy were great with communication and the cabin itself was beautiful! It had everything we needed for the weekend and the location is close to many nearby attractions. Book your stay at Mapletree Cabin.. you won't regret it! "
United States
Miguel D.
The price is ￥71,663
￥130,625 total
includes taxes & fees
Jun 3 - Jun 4
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
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 Town of Southold Town Hotel Reviews

The Shoals Suites and Slips

The Shoals Suites and Slips

10/10 Excellent
"We had such a beautiful stay! Can't wait to return!"
Eleni 1-night trip
Posted 1 hour ago
The Shoals Suites and Slips

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