A white colonial-style house with a green roof and a lighthouse tower.

Vacation Rentals in Town of Southold Town

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Our top choices for Town of Southold Town vacation rentals

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (30 reviews)
"Great stay & great staff!"
United States
James
The price is ¥60,477
¥69,096 total
includes taxes & fees
Jul 28 - Jul 29
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (271 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is ¥66,864
¥83,417 total
includes taxes & fees
Jul 29 - Jul 30
Cliffside Resort Condominiums

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 ¥66,127
¥93,839 total
includes taxes & fees
Jul 19 - Jul 20
American Beech in Greenport - Petite King Room 7

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 ¥232,304
¥348,186 total
includes taxes & fees
Aug 9 - Aug 10
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 ¥72,940
¥102,639 total
includes taxes & fees
Jul 16 - Jul 17
American Beech in Greenport - Deluxe King 6

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (47 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ¥24,709
¥43,987 total
includes taxes & fees
Jul 21 - Jul 22
1-bedroom cottage with Grove Beach 🏖️ access.

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, (42 reviews)
"We had a wonderful stay! The place was lovely, very clean, and exactly as described. Deb & Paul were great—friendly, responsive, and made everything easy for us. We’d definitely stay here again!"
United States
Francesca M.
The price is ¥19,478
¥38,280 total
includes taxes & fees
Jul 16 - Jul 17
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (9 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is ¥21,827
¥32,053 total
includes taxes & fees
Jul 19 - Jul 20
The Tiny Cottage & Mini Farm

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (37 reviews)
"Nice stay"
United States
WINFOR
The price is ¥26,192
¥49,078 total
includes taxes & fees
Jul 15 - Jul 16
Peaceful Oasis Steps from Mohegan Sun

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely adorable. Would stay again!!"
United States
Logan
The price is ¥14,697
¥32,456 total
includes taxes & fees
Jul 15 - Jul 16
A Mystic Stay as Sweet as Apple Pie!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (11 reviews)
"great place to stay"
United States
christopher
The price is ¥21,119
¥52,553 total
includes taxes & fees
Jul 15 - Jul 16
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.6 out of 10, Exceptional, (57 reviews)
"It was great ocation for a weekend get away with friends to Mohegan Sun"
United States
Teresa M.
The price is ¥22,845
¥50,201 total
includes taxes & fees
Jul 21 - Jul 22
Cozy, comfy,quiet &close to casinos

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)
"Everything was great location, cleanliness, and parking. Enjoyed the stay. Would recommend to anyone looking for a cozy get away!!"
United States
Timothy E.
The price is ¥22,312
¥53,791 total
includes taxes & fees
Jul 15 - Jul 16
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

Cozy Corner, by the Spa

Cozy Corner, by the Spa
Norwich
9.6 out of 10, Exceptional, (11 reviews)
"Very nice property, perfect for a long weekend!"
United States
Troy
The price is ¥27,146
¥60,806 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Corner, by the Spa

3 bed apartment, 5 mi to Mohegan/10 to Foxwoods

3 bed apartment, 5 mi to Mohegan/10 to Foxwoods
Laurel Hill
9.6 out of 10, Exceptional, (44 reviews)
"Enjoyed our stay, plenty of room and quiet. Had everything we needed and more. I will rent again for sure."
United States
chad m.
The price is ¥15,279
¥29,172 total
includes taxes & fees
Jul 22 - Jul 23
3 bed apartment, 5 mi to Mohegan/10 to Foxwoods

Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (77 reviews)
"Spacious"
United States
Mehul
The price is ¥21,018
¥37,186 total
includes taxes & fees
Jul 19 - Jul 20
Spacious 2 Bedroom apartment close to Yale Bowl

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (12 reviews)
"Parking was easy and the room was the right siz."
United States
Vicente B.
The price is ¥17,461
¥23,314 total
includes taxes & fees
Jul 19 - Jul 20
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath

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, (184 reviews)
"Fantastic location, great stay as always. Perfect for a weekend getaway."
United States
Jaime M.
The price is ¥20,210
¥47,008 total
includes taxes & fees
Aug 11 - Aug 12
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (17 reviews)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is ¥28,634
¥62,679 total
includes taxes & fees
Aug 12 - Aug 13
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa

Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
Norwich
10.0 out of 10, Exceptional, (16 reviews)
"We had a wonderful stay, host thought of all the little details."
United States
Jessica M.
The price is ¥30,866
¥57,873 total
includes taxes & fees
Jul 28 - Jul 29
Luxe Villa- mins from Mohegan Sun with fireplace, jacuzzi, sauna/pools, and spa
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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