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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 216 Cottages in Southold with updated reviews, rates, and availability.

Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (66)
"Enjoyed our stay very much. Place is beautiful, clean, hosts cannot b nicer. Definitely hope to return "
Fairy Tale Guest Cottage in Magic Garden by Pool
Sweet Cottage in Beach Community
Beach nearby, sun loungers, beach towels

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (6)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (25)
"We had a wonderful time for our two day stay, very private and quiet spot tucked away."
Location and views! Located directly on Shinnecock Bay!
Beach Cottage
Fridge, microwave, oven, stovetop

Beach Cottage

10.0 out of 10, Exceptional, (5)
"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 757
AED 1,637 total
includes taxes & fees
8 Jun - 9 Jun
Beach Cottage
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
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
On the beach, sun loungers, beach towels

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (70)
"Very enjoyable- we've booked already for next summer!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
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
Direct waterfront renovated cottage.
TV, books

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (73)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Exterior

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

10.0 out of 10, Exceptional, (71)
"Perfect and cozy home base for visiting with family!"
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Miscellaneous

Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more

10.0 out of 10, Exceptional, (2)
"Wonderful stay in a remodeled stone house. Host was great and the house is very comfortable. We really enjoyed the beautifully restored building and all the touches throughout. "
The price is AED 1,157
AED 1,959 total
includes taxes & fees
5 Jun - 6 Jun
Clinton's Hidden Secret Renovated 2-bedroom Stonehouse with WiFi, AC and more
Charming Old Lyme Cottage, Steps to Private Beach!
Coffee/tea maker

Charming Old Lyme Cottage, Steps to Private Beach!

7.8 out of 10, Good, (8)
"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!
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, (26)
"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
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
Inviting 3BR Beachfront Cottage in Hawk's Nest – Summer Escape Awaits!
Beach

Inviting 3BR Beachfront Cottage in Hawk's Nest – Summer Escape Awaits!

Inviting 3BR Beachfront Cottage in Hawk's Nest – Summer Escape Awaits!
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Fridge, microwave, oven, stovetop

A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve

10.0 out of 10, Exceptional, (2)
"This was an amazing place to stay. Beautiful property and EXCELLENT hosts! Thank you!"
A Perfect Getaway. Direct assess to the 1000 acre Old Saybrook Essex Preserve
Fabulous Waterfront Property in the Heart of Wine Country
Sun loungers, beach towels

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (174)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country
Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Sun loungers

Direct LI sound waterfront cottage, one level living in Hawks Nest Beach

Direct LI sound waterfront cottage, one level living in Hawks Nest Beach
Sabbatical a Private guest cottage in Sag Harbor
Exterior

Sabbatical a Private guest cottage in Sag Harbor

9.6 out of 10, Exceptional, (9)
"I can’t thank enough our hostess Susan for her amazing hospitality and kindness! I strongly recommend her place to stay for vacation!"
Sabbatical a Private guest cottage in Sag Harbor
Ritz - East Hampton Cottage On The Water
Smart TV

Ritz - East Hampton Cottage On The Water

10.0 out of 10, Exceptional, (6)
"We enjoyed our time in the Ritz. It’s a great cottage surrounded by waterfront activities. The host was accommodating and welcoming."
Ritz - East Hampton Cottage On The Water
1930s Waterfront Cottage on Tuttle's Point
Beach nearby, sun loungers

1930s Waterfront Cottage on Tuttle's Point

9.8 out of 10, Exceptional, (28)
"We had a wonderful stay! The kitchen was well outfitted and the beach was perfect for our little grandson. Great kayaking, biking, hiking and of course, eating! Backyard and porch were awesome."
1930s Waterfront Cottage on Tuttle's Point
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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