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Holiday Rentals in Town of Southold Town

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Our top choices for Town of Southold Town holiday rentals

Terrace/patio
American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €260
includes taxes & fees
20 Jan - 21 Jan
American Beech in Greenport - Petite King Room 7
Fridge, microwave, stovetop, dishwasher
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

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Greenport
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
The price is €452
includes taxes & fees
7 Jan - 8 Jan
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all

Charming Northfork Townhouse- walk to all
Greenport
10.0 out of 10, Exceptional, (5)
"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 €569
includes taxes & fees
7 Jan - 8 Jan
Charming Northfork Townhouse- walk to all
Property grounds
Beachfront Greenport Villa

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.6 out of 10, Exceptional, (10)
"We came for a girls trip and this property was perfect, had beautiful views and was close to everything...we very much enjoyed our stay!"
United States
Melissa F.
Beachfront Greenport Villa
Terrace/patio
Beautifully farmhouse

Beautifully farmhouse

Beautifully farmhouse
Southold
10.0 out of 10, Exceptional, (3)
"good experience"
United States
Anonymous traveller
The price is €1,025
includes taxes & fees
5 Jan - 6 Jan
Beautifully farmhouse
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated

Northfork Townhouse- walk to all/ newly renovated
Greenport
9.6 out of 10, Exceptional, (9)
"What a wonderful spot! We could walk to town, and a beach. We loved our stay in Greenport! "
United States
Laura B.
Northfork Townhouse- walk to all/ newly renovated
Property grounds
American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6

American Beech in Greenport - Deluxe King 6
Greenport
2.0 out of 10, (1)
"Not as advertised. Very disappointed "
United States
Jeffrey
American Beech in Greenport - Deluxe King 6
Front of property – evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1276)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is €151
includes taxes & fees
5 Jan - 6 Jan
Montauk Manor
Exterior
The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
2.0 star property
Oakdale,
10.0 out of 10, Exceptional, (2)
"Cottage was perfect! The fresh eggs given to us by the host made for an awesome breakfast! The host was great! My 2 energetic boys loved every animal. The host made sure to take my boys through every fence/gate there was to get my boys front and center with the animals. This isn’t just about money him seeing my boys smile and run around with the animals definitely made his day! Left about an hour ago and my boys already asked 17 times when we are going back! "
United States
jeff
The price is €114
includes taxes & fees
4 Jan - 5 Jan
The Tiny Cottage at Clem & Clyde's
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is €171
includes taxes & fees
12 Jan - 13 Jan
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds
Lakeside cottage ON the water with beautiful views up the lake!

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, (192)
"There were stunning views, it was very relaxing, and we had excellent communication with the host. We couldn’t be happier, it was perfect! Kayaking was the best part. Plenty to see and do in the area as well."
United States
Heather S.
The price is €235
includes taxes & fees
4 Jan - 5 Jan
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

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, (27)
"Everything was perfect! Great location, easy check in/out, great amenities in room, and super comfy bed. "
United States
Paul S.
The price is €173
includes taxes & fees
3 Jan - 4 Jan
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Microwave, stovetop, coffee/tea maker, toaster
Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium

Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium

Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium
Stonington
10.0 out of 10, Exceptional, (10)
"Nice location, easy access to downtown Mystic. Nice compliment of amenities. "
United States
Karen B.
The price is €170
includes taxes & fees
25 Jan - 26 Jan
Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium
Outdoor dining
Lakeside cottage overhanging the water, beautiful window views across the lake

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, (220)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is €227
includes taxes & fees
5 Jan - 6 Jan
Lakeside cottage overhanging the water, beautiful window views across the lake
Fridge, microwave, oven, stovetop
Super Cute & Cozy Apartment in Downtown Mystic!

Super Cute & Cozy Apartment in Downtown Mystic!

Super Cute & Cozy Apartment in Downtown Mystic!
Mystic
9.6 out of 10, Exceptional, (82)
"Beautiful, cozy, little apartment walking distance from downtown Mystic! Well kept and perfect for a quick 2 night trip!Thank you - would definitely stay here again! "
United States
Clayton H.
The price is €150
includes taxes & fees
5 Jan - 6 Jan
Super Cute & Cozy Apartment in Downtown Mystic!
Property grounds
A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
2.0 star property
Old Mystic
10.0 out of 10, Exceptional, (7)
"Loved the personal touches!"
United States
Jenny
The price is €190
includes taxes & fees
5 Jan - 6 Jan
A Mystic Stay as Sweet as Apple Pie!
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is €160
includes taxes & fees
10 Jan - 11 Jan
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (16)
"Great property, beautiful grounds and appointed as described! Owners were great to work with and flexible. "
United States
Bill M.
The price is €221
includes taxes & fees
4 Jan - 5 Jan
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
1 bedroom, WiFi, bed sheets
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

Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
New London
10.0 out of 10, Exceptional, (7)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
The price is €107
includes taxes & fees
21 Jan - 22 Jan
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €322
includes taxes & fees
5 Jan - 6 Jan
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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 Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great check in experience. Very nice room"
Christopher 2-night trip
Posted 5 days ago
The Harbor Front Inn

Find out more about Town of Southold Town

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