Vacation Rentals in Town of Southold Town

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Our top choices for Town of Southold Town vacation rentals

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is ¥29,349
¥33,531 total
includes taxes & fees
Apr 28 - Apr 29
North Fork Cottages & RV Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is ¥26,715
¥37,448 total
includes taxes & fees
May 11 - May 12
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 ¥26,935
¥42,430 total
includes taxes & fees
Apr 27 - Apr 28
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 ¥55,225
¥109,527 total
includes taxes & fees
Apr 27 - Apr 28
Northfork Townhouse walk to all

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.6 out of 10, Exceptional, (10 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 ¥50,922
¥103,884 total
includes taxes & fees
Apr 27 - Apr 28
Renovated 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 ¥64,549
¥124,734 total
includes taxes & fees
May 12 - May 13
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to 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 ¥31,717
¥48,803 total
includes taxes & fees
Apr 27 - Apr 28
American Beech in Greenport - Deluxe King 6

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,332 reviews)
"Incredible place to stay "
United States
melissa
Montauk Manor

The Tiny Cottage on The Ranch

The Tiny Cottage on The Ranch
Oakdale,
10.0 out of 10, Exceptional, (7 reviews)
"We were looking for a place to stay while in town for a volleyball tournament. This space worked out perfectly. We will be back! Next time hopefully we’ll have time to enjoy the farm. Thank you!"
United States
Rebecca N.
The price is ¥14,201
¥19,520 total
includes taxes & fees
Apr 28 - Apr 29
The Tiny Cottage on The Ranch

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is ¥23,625
¥31,327 total
includes taxes & fees
Apr 27 - Apr 28
Windward Shores Ocean Resort

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ¥12,766
¥28,683 total
includes taxes & fees
Apr 28 - Apr 29
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, (174 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 ¥15,141
¥40,204 total
includes taxes & fees
Apr 30 - May 1
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

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, (36 reviews)
"Absolutely adorable! Beautiful view from our window. Quaint decor and every little detail thought of. Loved our stay! "
United States
Randolph
The price is ¥11,987
¥28,886 total
includes taxes & fees
Apr 27 - Apr 28
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 ¥13,029
¥30,244 total
includes taxes & fees
Apr 27 - Apr 28
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, (49 reviews)
"Great location"
United States
Jeff F.
The price is ¥15,348
¥35,063 total
includes taxes & fees
Apr 28 - Apr 29
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Easy Beach Access! Classic New London Charmer

Easy Beach Access! Classic New London Charmer
3.5 star property
New London
The price is ¥15,619
¥56,639 total
includes taxes & fees
May 14 - May 15
Easy Beach Access! Classic New London Charmer

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 ¥25,102
¥51,102 total
includes taxes & fees
Apr 27 - Apr 28
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (48 reviews)
"Small place good for an individual or couple clean and as described."
United States
Anonymous traveler
The price is ¥19,978
¥51,503 total
includes taxes & fees
Apr 27 - Apr 28
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is ¥24,823
¥33,553 total
includes taxes & fees
May 17 - May 18
Driftwood Resort

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is ¥19,718
¥40,477 total
includes taxes & fees
Apr 28 - Apr 29
Freeboard at Soundview · Beach+Ocean+Sunrise
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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