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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 212 Cottages in Southold with updated reviews, rates, and availability.

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Living area

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC

Charming 3-bedroom cottage in Old Saybrook with WiFi and AC
Charming 3-bedroom cottage short walk to Chalker Beach
Smart TV, books

Charming 3-bedroom cottage short walk to Chalker Beach

Charming 3-bedroom cottage short walk to Chalker Beach
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (25)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AED 459
AED 728 total
includes taxes & fees
15 May - 16 May
1-bedroom cottage with Grove Beach 🏖️ access.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Property grounds

The gardners Cottage 1 mile from long Island Sound - pet friendly

10.0 out of 10, Exceptional, (13)
"Property is charming, beautifully decorated, clean. Host was very responsiveand even shared produce from her lovely garden! We hope to return."
The gardners Cottage 1 mile from long Island Sound - pet friendly
Enchanted Waterfront Cottage
Smart TV, fireplace, books

Enchanted Waterfront Cottage

9.0 out of 10, Wonderful, (19)
"The location was perfect. Very comfortable."
Enchanted Waterfront Cottage
Orient Village — Historic Bayfront Cottage — 2025 Season
Exterior

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (20)
"We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!"
Orient Village — Historic Bayfront Cottage — 2025 Season
Hampton Cottage.
Smart TV

Hampton Cottage.

10.0 out of 10, Exceptional, (4)
"charming small cottage, very fresh, crisp, and comfortable! 100% redone, everything is brand new! we might have been the first guest. good location for Hamptons travel & shopping & beaches fun restaurants & music nearby, Cowfish, Roomba, Canal Cafe, Francesco Pizza-Gelato. Mrs and I had a wonderful time, cheers!"
Hampton Cottage.
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Miscellaneous

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (91)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (24)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Beach nearby, sun loungers, beach towels

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (108)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Sun loungers, beach towels

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.4 out of 10, Exceptional, (36)
"Lovely cottage beautifully decorated, close to restaurants, farm stands, and food stores. A least a 15 to 20 minute walk to the beach."
The price is AED 731
AED 1,662 total
includes taxes & fees
18 May - 19 May
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

8.6 out of 10, Excellent, (7)
"The location and property were perfect for our stay. Homeowner was very accommodating. Can’t wait to go back!!!!"
Charming Old Lyme Cottage, Steps to Private Beach!
Charming Westbrook Cottage, Steps to Private Beach
Microwave, coffee/tea maker, toaster, cookware/dishes/utensils

Charming Westbrook Cottage, Steps to Private Beach

9.6 out of 10, Exceptional, (4)
"Had a great stay!"
Charming Westbrook Cottage, Steps to Private Beach
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (70)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Beach duplex—2 full homes with private access, backyard, and ocean views!
Beach nearby, sun loungers

Beach duplex—2 full homes with private access, backyard, and ocean views!

10.0 out of 10, Exceptional, (15)
" Very clean, plenty of room for multi generational family and the beach was very relaxing. Will stay again."
Beach duplex—2 full homes with private access, backyard, and ocean views!
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach nearby, sun loungers, beach towels

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (25)
"The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!"
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (71)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach nearby

'Grandma's Cottage' w/ Sunroom: Walk to Beach

8.0 out of 10, Very Good, (3)
"Terrific location. 1 block from the beach."
'Grandma's Cottage' w/ Sunroom: Walk to Beach
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (4)
"The cottage was very comfortable and had everything that I needed. The hosts were very attentive. The location was perfect; a quiet area just one block from a private beach. I would definitely stay again."
The price is AED 665
AED 1,521 total
includes taxes & fees
19 May - 20 May
Beach Cottage
Hamptons Vacation Rental w/ Seasonal Pool!
Fridge, microwave, stovetop, dishwasher

Hamptons Vacation Rental w/ Seasonal Pool!

10.0 out of 10, Exceptional, (5)
"We really enjoyed the place. Very nice, very clean. Had a million things that people never think of while staying away at a random place for a vacation house."
Hamptons Vacation Rental w/ Seasonal Pool!
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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Other property types in Southold

North Fork 7 Bedroom Farmhouse Escape
Beach nearby

North Fork 7 Bedroom Farmhouse Escape

3.0 star property
9.4 out of 10, Exceptional, (3)
"Nice property, extremely helpful Owner. Great kitchen"
North Fork 7 Bedroom Farmhouse Escape
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (283)
"Love the ocean view from the balcony"
The price is AED 565
AED 725 total
includes taxes & fees
12 May - 13 May
Windward Shores Ocean Resort
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (214)
"Great place. "
The price is AED 769
AED 1,038 total
includes taxes & fees
26 May - 27 May
Cliffside Resort Condominiums
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.