Holiday Rentals in Town of Southold Town

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Our top choices for Town of Southold Town holiday rentals

Cottage, 2 Bedrooms, Patio

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is €181
includes taxes & fees
7 Apr - 8 Apr
North Fork Cottages & RV Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is €209
includes taxes & fees
2 Apr - 3 Apr
Cliffside Resort Condominiums
Terrace/patio

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is €229
includes taxes & fees
5 Apr - 6 Apr
American Beech in Greenport - Petite King Room 7
Smart TV, fireplace

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.
Renovated Townhouse walk to all
Dining

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.
Northfork Townhouse walk to all
Smart TV, books

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 €635
includes taxes & fees
15 Apr - 16 Apr
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
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.
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
American Beech in Greenport - Deluxe King 6
Exterior

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 €286
includes taxes & fees
12 Apr - 13 Apr
Cozy Lakefront Tiny House
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,309 reviews)
"Great property "
United States
brian
The price is €166
includes taxes & fees
6 Apr - 7 Apr
Montauk Manor
Smart TV, books

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)
"Very welcoming, clean, comfortable and responsive. It was perfectly what we needed for a little get away. "
United States
Sylvia R.
The price is €217
includes taxes & fees
5 Apr - 6 Apr
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Living area

The Tiny Cottage at Clem & Clyde's

The Tiny Cottage at Clem & Clyde's
Oakdale,
10.0 out of 10, Exceptional, (7 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 €133
includes taxes & fees
5 Apr - 6 Apr
The Tiny Cottage at Clem & Clyde's
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, (8 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 €182
includes taxes & fees
9 Apr - 10 Apr
A Mystic Stay as Sweet as Apple Pie!
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is €170
includes taxes & fees
6 Apr - 7 Apr
Windward Shores Ocean Resort
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, (34 reviews)
"Absolutely adorable! Beautiful view from our window. Quaint decor and every little detail thought of. Loved our stay! "
United States
Randolph
The price is €174
includes taxes & fees
5 Apr - 6 Apr
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC
Exterior

Peaceful Oasis Steps from Mohegan Sun

Peaceful Oasis Steps from Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (31 reviews)
"Welcoming and felt like home! Extremely clean and would love to stay in this exact location again!!! "
United States
Sandra D.
The price is €265
includes taxes & fees
2 Apr - 3 Apr
Peaceful Oasis Steps from Mohegan Sun
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, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is €160
includes taxes & fees
2 Apr - 3 Apr
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (35 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is €274
includes taxes & fees
10 Apr - 11 Apr
Walk To Goodspeed Opera House!
Interior

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (18 reviews)
"Wonderful place with a great location! Fantastic communication!"
United States
Cary H.
The price is €264
includes taxes & fees
7 Apr - 8 Apr
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Fridge, microwave, oven, stovetop

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Stonington
10.0 out of 10, Exceptional, (1 review)
"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...
United States
Kerri P.
The price is €279
includes taxes & fees
12 Apr - 13 Apr
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
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

Sound View Greenport

Sound View Greenport

8/10 Good
"it was ok"
angelo 1-night trip
Posted 2 days ago
Sound View Greenport

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Holiday Homes in Town of Southold Town

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