A white colonial-style house with a green roof and a lighthouse tower.

Town of Southold Town Holiday Rentals

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Our top choices for Town of Southold Town holiday rentals

Flat-screen TV

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is HK$2,521
HK$2,881 total
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
Terrace/patio

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (283 reviews)
"Great place!"
United States
Christine
The price is HK$2,405
HK$3,447 total
includes taxes & fees
7 Sept - 8 Sept
Cliffside Resort Condominiums
Sun-loungers, beach towels

3. The SandPiper

The SandPiper
Pipes Cove
9.6 out of 10, Exceptional, (47 reviews)
"Lovely place, very clean, host was very responsive. Thanks so much!"
United States
Marie H.
The price is HK$1,530
HK$2,950 total
includes taxes & fees
10 Sept - 11 Sept
The SandPiper
Sun-loungers, beach towels

4. Aqua Vista

Aqua Vista
Pipes Cove
10.0 out of 10, Exceptional, (41 reviews)
"Nice clean space, well appointed and easy walking access to downtown area."
United States
Molly G.
The price is HK$1,530
HK$2,950 total
includes taxes & fees
8 Sept - 9 Sept
Aqua Vista
Beach

5. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (22 reviews)
"Close to the train, beach and restaurant, very convenient on foot"
United States
Nigel
The price is HK$1,530
HK$3,012 total
includes taxes & fees
13 Sept - 14 Sept
Harbor Heights
Sun-loungers, beach towels

6. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Pipes Cove
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay!! "
United States
Callie E.
The price is HK$1,923
HK$4,052 total
includes taxes & fees
7 Sept - 8 Sept
Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office
Terrace/patio

7. American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.4 out of 10, Exceptional, (6 reviews)
"Great place! So nice."
United States
Paul F.
The price is HK$2,425
HK$3,523 total
includes taxes & fees
7 Sept - 8 Sept
American Beech in Greenport - Petite King Room 7
Beach

8. Beach Block Hideaway

Beach Block Hideaway
Pipes Cove
10.0 out of 10, Exceptional, (8 reviews)
"Everything about Beach Block Hideaway was perfect! The house was absolutely immaculate, the kitchen well stocked with plenty of kitchenware, beds very comfortable. Easy walk to town. We have stayed at a number of homes when visiting Greenport over the years but this place is truly the best - highly recommend! "
United States
maureen f.
The price is HK$2,315
HK$4,303 total
includes taxes & fees
8 Sept - 9 Sept
Beach Block Hideaway
Smart TV, books

9. 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$5,383
HK$9,028 total
includes taxes & fees
9 Sept - 10 Sept
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Property grounds

10. Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (13 reviews)
"yes the house had everything we needed"
United States
patricia m.
The price is HK$7,451
HK$11,731 total
includes taxes & fees
10 Sept - 11 Sept
Beachfront Greenport Villa
Property grounds

11. 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$2,817
HK$4,034 total
includes taxes & fees
7 Sept - 8 Sept
American Beech in Greenport - Deluxe King 6
1 bedroom, desk, iron/ironing board, travel cot

12. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (52 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$883
HK$1,744 total
includes taxes & fees
15 Sept - 16 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
Free WiFi, individually decorated, individually furnished, bed sheets

13. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (246 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is HK$1,838
HK$2,355 total
includes taxes & fees
13 Sept - 14 Sept
Driftwood Resort
Outdoor dining

14. Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Norwich
9.6 out of 10, Exceptional, (61 reviews)
"Beautfil and convenient place. We stayed just one night and the location is perfect since it's just by the Spa."
United States
Aura
The price is HK$1,130
HK$2,227 total
includes taxes & fees
8 Sept - 9 Sept
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Lobby

15. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,387 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is HK$2,331
HK$2,816 total
includes taxes & fees
7 Sept - 8 Sept
Montauk Manor
Smart TV

16. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (10 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is HK$953
HK$1,253 total
includes taxes & fees
17 Aug - 18 Aug
The Tiny Cottage & Mini Farm
Interior

17. Cozy Studio: Indoor Hot Tub & Inground Pool Access

Cozy Studio: Indoor Hot Tub & Inground Pool Access
3.0 star property
Montville
10.0 out of 10, Exceptional, (1 review)
"Everything from the price,location,tranquility, and the host Allen was awesome. We would go back in a heartbeat. Montville is beautiful."
United States
Eduardo
The price is HK$1,491
HK$3,370 total
includes taxes & fees
26 Aug - 27 Aug
Cozy Studio: Indoor Hot Tub & Inground Pool Access
1 bedroom, WiFi, bed sheets

18. 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, (13 reviews)
"Parking was easy and the room was the right siz."
United States
Vicente B.
The price is HK$847
HK$1,132 total
includes taxes & fees
17 Aug - 18 Aug
Cozy spacious bedroom with king size bed, only half mile to Rt.95, private bath
A heated pool

19. Cozy Corner, by the Spa

Cozy Corner, by the Spa
Norwich
9.6 out of 10, Exceptional, (11 reviews)
"Very nice property, perfect for a long weekend!"
United States
Troy
The price is HK$966
HK$2,594 total
includes taxes & fees
8 Sept - 9 Sept
Cozy Corner, by the Spa
Property grounds

20. A Mystic Stay as Sweet as Apple Pie!

A Mystic Stay as Sweet as Apple Pie!
Old Mystic
10.0 out of 10, Exceptional, (11 reviews)
"Absolutely adorable. Would stay again!!"
United States
Logan
The price is HK$949
HK$1,890 total
includes taxes & fees
17 Aug - 18 Aug
A Mystic Stay as Sweet as Apple Pie!
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Very excellent boutique hotel right on Main st. Beautiful garden for relaxing. Perfect location, friendly staff"
shaun 1-night trip
Posted 20 hours ago
Zey Hotel