A calm lake with a forest in the background during sunset.

Search Southold Cottage Rentals from CA $352

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Southold cottages

Balcony

1. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (41 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is CA $691
CA $789 total
includes taxes & fees
Aug 31 - Sep 1
North Fork Resort
Exterior

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

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (25 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is CA $350
CA $584 total
includes taxes & fees
Aug 20 - Aug 21
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

3. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $192
CA $352 total
includes taxes & fees
Aug 12 - Aug 13
1-bedroom cottage with Grove Beach 🏖️ access.
Exterior

4. Seabreeze #3 Cozy Cottage steps to the beach

Seabreeze #3 Cozy Cottage steps to the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is CA $525
CA $1,142 total
includes taxes & fees
Aug 9 - Aug 10
Seabreeze #3 Cozy Cottage steps to the beach
Exterior

5. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is CA $221
CA $512 total
includes taxes & fees
Aug 24 - Aug 25
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Exterior

6. Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (13 reviews)
"An absolutely adorable and cozy cottage steps from a lovely beach. The location is great, beds were so comfortable and everything was clean and well designed. Would definitely stay here again"
United States
Maria M.
The price is CA $559
CA $992 total
includes taxes & fees
Aug 31 - Sep 1
Beach Cottage, private beach and pass
Exterior

7. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (50 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is CA $818
CA $1,310 total
includes taxes & fees
Aug 25 - Aug 26
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Exterior

8. Seabreeze 4 Charming Cottage footsteps to beach

Seabreeze 4 Charming Cottage footsteps to beach
Hampton Bays
9.4 out of 10, Exceptional, (6 reviews)
"Great stay. Would stay again. "
United States
Weston B.
The price is CA $232
CA $792 total
includes taxes & fees
Aug 4 - Aug 5
Seabreeze 4 Charming Cottage footsteps to beach
Exterior

9. Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
Hampton Bays
9.8 out of 10, Exceptional, (7 reviews)
"Had a great stay."
United States
Cameron T.
The price is CA $1,363
CA $2,370 total
includes taxes & fees
Aug 5 - Aug 6
Hamptons Vacation Rental w/ Saltwater Pool
Cottage (3 Bedrooms) | Interior

10. Hamptons Vacation Rental w/ Saltwater Pool

Hamptons Vacation Rental w/ Saltwater Pool
3.0 star property
Hampton Bays
The price is CA $1,584
CA $2,398 total
includes taxes & fees
Aug 5 - Aug 6
Hamptons Vacation Rental w/ Saltwater 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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Top Southold Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Kind and helpful staff. Didn't have a place to refill our water bottles but she gave us some complimentary water bottles. The room was comfortable and clean. There was a smell in the room and I couldn't tell if it was from cleaning supplies or the AC or what. I'm usually very sensitive to smells but thankfully whatever it was we got used to it and it didn't bother me. Appreciated the affordable price."
Circe 2-night trip
Posted 8 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Southold

Southold Cottages information

Number of reviews
186
Accommodation
221 Cottages
Lowest Price
CA $352
Highest Price
CA $2,398

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