Town of Southold Town Holiday Rentals

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Our top choices for Town of Southold Town holiday rentals

Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is HK$1,577
HK$2,142 total
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (18 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,326
HK$2,657 total
includes taxes & fees
16 Jun - 17 Jun
North Fork Resort
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 HK$1,637
HK$2,487 total
includes taxes & fees
21 May - 22 May
American Beech in Greenport - Petite King Room 7
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.
The price is HK$2,537
HK$5,153 total
includes taxes & fees
20 May - 21 May
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 HK$3,892
HK$7,121 total
includes taxes & fees
3 Jun - 4 Jun
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Smart TV, fireplace

Renovated Townhouse walk to all

Renovated Townhouse walk to all
Greenport
9.8 out of 10, Exceptional, (11 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 HK$2,784
HK$5,480 total
includes taxes & fees
20 May - 21 May
Renovated Townhouse walk to all
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 HK$5,638
HK$9,590 total
includes taxes & fees
27 May - 28 May
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 HK$1,950
HK$2,881 total
includes taxes & fees
20 May - 21 May
American Beech in Greenport - Deluxe King 6
1 bedroom, bed sheets

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,515
HK$2,321 total
includes taxes & fees
21 May - 22 May
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,346 reviews)
"Had a wonderful stay"
United States
Meghan
The price is HK$1,269
HK$1,603 total
includes taxes & fees
25 May - 26 May
Montauk Manor
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, (313 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is HK$1,333
HK$1,736 total
includes taxes & fees
21 May - 22 May
Windward Shores Ocean Resort
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (238 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is HK$1,220
HK$1,648 total
includes taxes & fees
20 May - 21 May
Driftwood Resort
Terrace/patio

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful view of the waters and lots ofcroom to relax."
United States
Omar
The price is HK$3,623
HK$7,298 total
includes taxes & fees
3 Jun - 4 Jun
Thames River Retreat · CT College+Casinos+USCGA
Terrace/patio

Tranquil Farmhouse Retreat

Tranquil Farmhouse Retreat
Montville
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay during the Thanksgiving holiday. We were able to enjoy the space of the house and the close proximity to Mohegan Sun."
United States
Allison R.
The price is HK$3,132
HK$6,582 total
includes taxes & fees
1 Jun - 2 Jun
Tranquil Farmhouse Retreat
Interior

Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage

Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (22 reviews)
"Cute, clean, and perfect little place for an overnight visit :)"
United States
Anonymous traveller
The price is HK$2,153
HK$2,790 total
includes taxes & fees
25 May - 26 May
Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
Beach nearby, sun-loungers, beach towels

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is HK$2,811
HK$5,146 total
includes taxes & fees
27 May - 28 May
Beach Cottage, private beach and pass
Interior

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun

Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun
Norwich
10.0 out of 10, Exceptional, (28 reviews)
"We loved our stay! Beautifully decorated, clean and spacious! We will definitely be back!"
United States
Theresa C.
The price is HK$1,614
HK$3,305 total
includes taxes & fees
24 May - 25 May
Newly Renovated Loft Villa at Norwich Spa, minutes to Mohegan Sun
Property grounds

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (56 reviews)
"Stayed here for Valentine's weekend with my wife and it was perfect! Gardner and Kathy were great with communication and the cabin itself was beautiful! It had everything we needed for the weekend and the location is close to many nearby attractions. Book your stay at Mapletree Cabin.. you won't regret it! "
United States
Miguel D.
The price is HK$3,915
HK$6,936 total
includes taxes & fees
3 Jun - 4 Jun
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Exterior

Brand new home close to Charlestown/Westerly beaches.

Brand new home close to Charlestown/Westerly beaches.
Westerly
9.8 out of 10, Exceptional, (42 reviews)
"THE PLACE WAS CLEAN AND THE OWNERS ARE VERY NICE."
United States
Veneice T.
The price is HK$2,819
HK$7,749 total
includes taxes & fees
26 May - 27 May
Brand new home close to Charlestown/Westerly beaches.
TV

#35 - Beautiful 3 BR Beach Haven

#35 - Beautiful 3 BR Beach Haven
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"Beautiful property! Just four houses from the beach and a beachfront restaurant. Very comfortable living areas. Well appointed kitchen with in unit washer and dryer. Host was prompt and clear with all communication. Off street parking with room for three vehicles. Too cold to use the outside lounging areas, but they look very nice as well. "
United States
Tim M.
The price is HK$2,086
HK$4,263 total
includes taxes & fees
22 May - 23 May
#35 - Beautiful 3 BR Beach Haven
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

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

10/10 Excellent
"We had a wonderful time! The cottage was exceptionally clean and comfortable! We'll definitely be going back!"
Lisa 2-night trip
Posted 11 hours ago
North Fork Cottages & RV Resort