Holiday Rentals in Town of Southold Town

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Our top choices for Town of Southold Town holiday rentals

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €171
includes taxes & fees
17 Feb - 18 Feb
American Beech in Greenport - Petite King Room 7

Cottage on Beach front Estate with Dockage .Walk to Village

Cottage on Beach front Estate with Dockage .Walk to Village
Pipes Cove
10.0 out of 10, Exceptional, (75 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is €292
includes taxes & fees
28 Feb - 1 Mar
Cottage on Beach front Estate with Dockage .Walk to Village

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons

Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
Southold
The price is €379
includes taxes & fees
1 Mar - 2 Mar
Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons

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 €514
includes taxes & fees
16 Feb - 17 Feb
Renovated Townhouse walk to all

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 €495
includes taxes & fees
16 Feb - 17 Feb
Northfork 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 €484
includes taxes & fees
18 Feb - 19 Feb
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Breakwater Estate… perfect for Large Group Getaways!

Breakwater Estate… perfect for Large Group Getaways!
Mattituck
10.0 out of 10, Exceptional, (35 reviews)
"Beautiful property. Great pool, We had a great time."
United States
william p.
The price is €1,043
includes taxes & fees
27 Feb - 28 Feb
Breakwater Estate… perfect for Large Group Getaways!

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 €204
includes taxes & fees
16 Feb - 17 Feb
American Beech in Greenport - Deluxe King 6

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is €221
includes taxes & fees
17 Feb - 18 Feb
Cozy Lakefront Tiny House

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,294 reviews)
"Nice pool, great restaurant "
United States
April
The price is €150
includes taxes & fees
16 Feb - 17 Feb
Montauk Manor

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (305 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is €150
includes taxes & fees
16 Feb - 17 Feb
Windward Shores Ocean Resort

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, (172 reviews)
"Perfect for our overnight needs."
United States
Kathleen C.
The price is €210
includes taxes & fees
12 Mar - 13 Mar
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
Oakdale,
10.0 out of 10, Exceptional, (6 reviews)
"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 €104
includes taxes & fees
16 Feb - 17 Feb
The Tiny Cottage at Clem & Clyde's

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is €180
includes taxes & fees
19 Feb - 20 Feb
The Stern at Soundview · Beach+Ocean+Sunrise

A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (7 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 €187
includes taxes & fees
16 Feb - 17 Feb
A Mystic Stay as Sweet as Apple Pie!

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (47 reviews)
"Small place good for an individual or couple clean and as described."
United States
Anonymous traveller
The price is €205
includes taxes & fees
10 Mar - 11 Mar
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

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, (9 reviews)
"Wonderful stay! Excellent host! Everything you need for a great weekend and then some. Highly recommended. "
United States
Robert I.
The price is €181
includes taxes & fees
16 Feb - 17 Feb
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

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, (41 reviews)
"We had an amazing stay, everything was perfect! Thank you so much, we would definitely stay again! "
United States
Kerri S.
The price is €272
includes taxes & fees
16 Feb - 17 Feb
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

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, (37 reviews)
"If going to either casino it is a short ride. It was just what we were looking for. "
United States
bonnie M.
The price is €160
includes taxes & fees
16 Feb - 17 Feb
3 bed apartment, 5 mi to Mohegan/10 to Foxwoods

Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!

Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
Ledyard
10.0 out of 10, Exceptional, (12 reviews)
"My husband and I stayed in the cottage with our fur baby and it was perfect. The cottage was very comfortable and very private."
United States
Kim S.
The price is €231
includes taxes & fees
16 Feb - 17 Feb
Plan Your Escape to the Cottage! Minutes to Mystic, Connecticut. This pet-friendly retreat has a private fenced-in rear garden patio. Your stay includes organic breakfast, firepit, hammock, and onsite hiking trails. Up to 2 well-behaved pets welcome!
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

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Holiday Homes in Town of Southold Town

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