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Vacation Homes in Orient

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10.0 out of 10, Exceptional, (8)
"Michael's cottage was incredibly well-appointed. The location to Southampton, Coopers Beach and neighboring townships made this very convenient for my trip. The true star of this cottage is the upstairs deck which was perfect for relaxing and stargazing. I will certainly return next summer. "
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Thames River Retreat · CT College+Casinos+USCGA

10.0 out of 10, Exceptional, (5)
"We found this home a perfect combination of being able to get away but also convenient to restaurants, stores, and activities. The view could not be beat and the house was clean and comfortable."
The price is SAR 444
SAR 1,832 total
includes taxes & fees
20 Jul - 21 Jul
Thames River Retreat · CT College+Casinos+USCGA

Charming 1845 Home in the Heart of Mystic – Walk to Everything!

9.8 out of 10, Exceptional, (149)
"Super time. Property is confidently located which made it easy to walk everywhere."
The price is SAR 986
SAR 1,756 total
includes taxes & fees
3 Aug - 4 Aug
Charming 1845 Home in the Heart of Mystic – Walk to Everything!

Sag Harbor Village Gem

10.0 out of 10, Exceptional, (42)
"Clean and friendly, great location"
Sag Harbor Village Gem

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

6.0 out of 10, (4)
"Really convenient location breakfast was good. Rooms were clean."
The price is SAR 315
SAR 437 total
includes taxes & fees
20 Jul - 21 Jul
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

9.8 out of 10, Exceptional, (156)
"Clean comfortable vintage property. Convenient to Stonington Borough, Mystic and Westerly."
The price is SAR 469
SAR 971 total
includes taxes & fees
16 Jul - 17 Jul
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is SAR 671
SAR 977 total
includes taxes & fees
11 Aug - 12 Aug
Shoreline Oasis

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (145)
"Had a nice time. The house was well furnished. "
Charming Historic House in Downtown Mystic

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (88)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

9.4 out of 10, Exceptional, (10)
"Great for families!"
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Walk to the beach from 4 Bedroom house in Amagansett - Private Beach Path Access

Another rental season is coming up.

10.0 out of 10, Exceptional, (15)
"Absolutely beautiful home with everything you need for an enjoyable vacation. The host was a pleasure to work with making sure we were comfortable with our accommodations. Definitely a great place to stay. "
Another rental season is coming up.

Regency Inn and Suites - Non Smoking King

7.0 out of 10, Good, (2)
"Roadway and parking could use some repairs"
The price is SAR 315
SAR 437 total
includes taxes & fees
20 Jul - 21 Jul
Regency Inn and Suites - Non Smoking King

Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

10.0 out of 10, Exceptional, (2)
"The property was exactly as posted. The host was great, super helpful and responsive. The pool was awesome for the kids. It was private and a wonderful stay in Sag Harbor. The town was cute and close. We would definitely stay again ! Thanks so much!"
The price is SAR 2,250
SAR 4,649 total
includes taxes & fees
20 Jul - 21 Jul
Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

The Cooper-Burke House

10.0 out of 10, Exceptional, (27)
"Nice location and house "
The Cooper-Burke House

Southampton Newly-renovated Home / Heated Pool!

10.0 out of 10, Exceptional, (28)
"We’ll kept - great layout, great backyard would love to go bakc"
Southampton Newly-renovated Home / Heated Pool!

The Seaport Bridgeman - All things Mystic steps from your door

10.0 out of 10, Exceptional, (21)
"We had a great stay. Highly recommended!"
The Seaport Bridgeman - All things Mystic steps from your door

Perfect beach house getaway within walking distance to the beach

8.6 out of 10, Excellent, (7)
"Great weekend getaway - close to the beaches and towns. Lovely little house with firepit and very quiet neighborhood."
Perfect beach house getaway within walking distance to the beach

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (45)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
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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