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Town of Southold Town Holiday Rentals

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Featured Town of Southold Town Holiday Rentals

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

Holiday Home in Greenport

9.0 out of 10, Wonderful, (4)
"Great job "
United States
emilio
The price is HK$1,393
HK$2,152 total
includes taxes & fees
8 Dec - 9 Dec
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

Cottage in 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 HK$1,767
HK$4,065 total
includes taxes & fees
10 Dec - 11 Dec
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Fridge, microwave, oven, stovetop
Charming Northfork Townhouse- walk to all

Holiday Home in 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 HK$2,530
HK$5,132 total
includes taxes & fees
8 Dec - 9 Dec
Charming Northfork Townhouse- walk to all
Property grounds
Beachfront Greenport Villa

Holiday Home in 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.
The price is HK$4,671
HK$8,236 total
includes taxes & fees
8 Dec - 9 Dec
Beachfront Greenport Villa
Fridge, microwave, oven, stovetop
Northfork Townhouse- walk to all/ newly renovated

Holiday Home in 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.
The price is HK$2,802
HK$5,488 total
includes taxes & fees
8 Dec - 9 Dec
Northfork Townhouse- walk to all/ newly renovated
Property grounds
American Beech in Greenport - Deluxe King 6

Holiday Home in Greenport

2.0 out of 10, (1)
"Not as advertised. Very disappointed "
United States
Jeffrey
The price is HK$1,783
HK$2,677 total
includes taxes & fees
8 Dec - 9 Dec
American Beech in Greenport - Deluxe King 6
Front of property – evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is HK$1,079
HK$1,385 total
includes taxes & fees
8 Dec - 9 Dec
Montauk Manor
Property grounds
Lakeside cottage ON the water with beautiful views up the lake!

Cottage in Ledyard

9.8 out of 10, Exceptional, (191)
"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 HK$679
HK$1,871 total
includes taxes & fees
10 Dec - 11 Dec
Lakeside cottage ON the water with beautiful views up the lake!
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
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 HK$592
HK$1,505 total
includes taxes & fees
3 Jan - 4 Jan 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Terrace/patio
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Apartment in Westerly

9.4 out of 10, Exceptional, (11)
"It was sweet, small but roomy for 2.A C was wonderful in the hot day. All provisions served us well. "
United States
Mary Alice B.
The price is HK$584
HK$967 total
includes taxes & fees
21 Dec - 22 Dec
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Outdoor dining
Lakeside cottage overhanging the water, beautiful window views across the lake

Cottage in Ledyard

9.8 out of 10, Exceptional, (217)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is HK$617
HK$1,694 total
includes taxes & fees
10 Dec - 11 Dec
Lakeside cottage overhanging the water, beautiful window views across the lake
Microwave, stovetop, coffee/tea maker, toaster
Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium

Apartment in 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 HK$592
HK$1,505 total
includes taxes & fees
6 Jan - 7 Jan 2026
Flemish Landing-#2 · walk Mystic-Train/EV Lvl-2 · aquarium
Property grounds
A Mystic Stay as Sweet as Apple Pie!

Holiday Home in Old Mystic

2.0 star property
10.0 out of 10, Exceptional, (7)
"Loved the personal touches!"
United States
Jenny
The price is HK$796
HK$1,685 total
includes taxes & fees
4 Jan - 5 Jan 2026
A Mystic Stay as Sweet as Apple Pie!
Fridge, microwave, oven, stovetop
Super Cute & Cozy Apartment in Downtown Mystic!

Apartment in Mystic

9.6 out of 10, Exceptional, (81)
"Intention of this place meant well. We felt safe and it was clean. Bed was super comfortable. The only downsides were the lack of AC that reached the bedroom and the dog smell from maybe earlier guests? There were many air purifiers for the pets but when we walked in that’s all we could smell. But host was kind and communicative. He left snacks and some waters for us. Again- place is very cute and a great location. "
United States
Brittani N.
The price is HK$490
HK$1,391 total
includes taxes & fees
10 Dec - 11 Dec
Super Cute & Cozy Apartment in Downtown Mystic!
Property grounds
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

Apartment in 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 HK$694
HK$1,551 total
includes taxes & fees
30 Dec - 31 Dec
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
1 bedroom, WiFi, bed sheets
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

Apartment in 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 HK$685
HK$944 total
includes taxes & fees
8 Dec - 9 Dec
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
Exterior detail
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage

Cottage in West Mystic

9.8 out of 10, Exceptional, (17)
"We had a wonderful time, great place which was like a small resort. Beautiful views and it was quiet and so peaceful there. We’re looking forward to staying again."
United States
Michael V.
The price is HK$1,316
HK$1,700 total
includes taxes & fees
8 Dec - 9 Dec
Harbor View Landing, Mystic CT - The Cove Waterfront Cottage
Beach nearby
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private

Holiday Home in Salem

10.0 out of 10, Exceptional, (5)
"Place is nice would stay again "
United States
nic
The price is HK$712
HK$2,768 total
includes taxes & fees
8 Dec - 9 Dec
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is HK$1,109
HK$2,436 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Property grounds
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

Villa in Norwich

9.8 out of 10, Exceptional, (47)
"Small but clean and cozy! Not impressed just another apartment. Spa and pool very nice. I would return. "
United States
Johnny B.
The price is HK$985
HK$1,981 total
includes taxes & fees
8 Dec - 9 Dec
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
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
"Monica really helped us out with our last-minute travel needs. She's a gem and so is this Inn and the North Fork in general. We'll be back."
John 1-night trip
Posted 21 hours ago
The Harbor Front Inn