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

Holiday Rentals in Town of Southold Town

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Our top choices for Town of Southold Town holiday rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (25 reviews)
"Great stay & great staff!"
United States
James
The price is €372
includes taxes & fees
27 Jul - 28 Jul
North Fork Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (263 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is €450
includes taxes & fees
7 Jul - 8 Jul
Cliffside Resort Condominiums
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 €486
includes taxes & fees
6 Jul - 7 Jul
American Beech in Greenport - Petite King Room 7
Fridge, microwave, oven, stovetop

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 €1,380
includes taxes & fees
15 Jul - 16 Jul
New Construction Greenport Pool House - 3 Blocks from 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 €561
includes taxes & fees
8 Jul - 9 Jul
American Beech in Greenport - Deluxe King 6
Smart TV

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 €144
includes taxes & fees
2 Jul - 3 Jul
The Tiny Cottage & Mini Farm
Smart TV

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, (43 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 €162
includes taxes & fees
9 Jul - 10 Jul
3 bed apartment, 5 mi to Mohegan/10 to Foxwoods
1 bedroom, desk, iron/ironing board, travel cot

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 €267
includes taxes & fees
27 Jul - 28 Jul
1-bedroom cottage with Grove Beach 🏖️ access.
Marina

Clean room w/ King bed/Private bathroom. Free Wifi free parking

Clean room w/ King bed/Private bathroom. Free Wifi free parking
New London
9.8 out of 10, Exceptional, (16 reviews)
"Stayed for two nights. Such a great location to the coast guard academy and lots of little restaurants and places to visit. Bill is a great host and very eager to provide a comfortable stay. "
United States
Julio J.
The price is €121
includes taxes & fees
2 Jul - 3 Jul
Clean room w/ King bed/Private bathroom. Free Wifi free parking
Exterior

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 €273
includes taxes & fees
8 Jul - 9 Jul
Peaceful Oasis Steps from Mohegan Sun
Exterior

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, (182 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 €260
includes taxes & fees
31 Jul - 1 Aug
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Terrace/patio

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, (12 reviews)
"Wonderful stay! Excellent host! Everything you need for a great weekend and then some. Highly recommended. "
United States
Robert I.
The price is €226
includes taxes & fees
2 Jul - 3 Jul
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Exterior

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 €385
includes taxes & fees
7 Jul - 8 Jul
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Smart TV

Cozy, comfy,quiet &close to casinos

Cozy, comfy,quiet &close to casinos
Montville
9.6 out of 10, Exceptional, (57 reviews)
"Clean home. Couldn’t be easier to get to Mohegan Sun! Very convenient."
United States
Angela
The price is €275
includes taxes & fees
7 Jul - 8 Jul
Cozy, comfy,quiet &close to casinos
Property grounds

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (10 reviews)
"Absolutely adorable. Would stay again!!"
United States
Logan
The price is €228
includes taxes & fees
8 Jul - 9 Jul
A Mystic Stay as Sweet as Apple Pie!
Dining

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, (76 reviews)
"Spacious"
United States
Mehul
The price is €208
includes taxes & fees
23 Jul - 24 Jul
Spacious 2 Bedroom apartment close to Yale Bowl
A heated pool

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 €336
includes taxes & fees
7 Jul - 8 Jul
Cozy Corner, by the Spa
Smart TV, offices, printers

Comfy Waterfront Walkout! Enjoy your own private terrace overlooking the Thames!

Comfy Waterfront Walkout! Enjoy your own private terrace overlooking the Thames!
Groton
9.8 out of 10, Exceptional, (111 reviews)
"The property was beautiful inside and outside. Very clean and very peaceful. The host was pleasant to communicate with and response time was prompt. I would book another stay without hesitation. "
United States
Stormy
The price is €291
includes taxes & fees
8 Jul - 9 Jul
Comfy Waterfront Walkout! Enjoy your own private terrace overlooking the Thames!
Outdoor dining

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 €326
includes taxes & fees
7 Jul - 8 Jul
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (8 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
The price is €455
includes taxes & fees
5 Jul - 6 Jul
Rogers Lake House (87) · CT College+Beach+USCGA
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

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

10/10 Excellent
"A must stay when in the area. Clay takes really good care of you! His pastries are amazing."
Ecaterini 3-night trip
Posted 16 hours ago
Stirling House Bed & Breakfast

Find out more about Town of Southold Town

Holiday Homes in Town of Southold Town

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