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Browse Select Sag Harbor Cottages

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

Charming 3-bedroom cottage short walk to Chalker Beach

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"
1-bedroom cottage with Grove Beach 🏖️ access.

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.

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 .

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!

9.2 out of 10, Wonderful, (23)
"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

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

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

10.0 out of 10, Exceptional, (3)
"Cozy cottage, good location, nice access to the Sound."
Charming Westbrook Cottage, Steps to Private Beach

Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

10.0 out of 10, Exceptional, (14)
" Very clean, plenty of room for multi generational family and the beach was very relaxing. Will stay again."
Beachside Twinhome: 2 Private Sides + Sunroom Escape for Friends & Family

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

'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

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!

Charming 3-bedroom cottage in fabulous Greenport

Charming 3-bedroom cottage in fabulous Greenport

Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

10.0 out of 10, Exceptional, (60)
"Wonderful stay! The hosts are friendly and communicative; the location is superb - so beautiful and you can smell the salt in the air; and the cottage was cozy and all that we needed. Thank you for a great stay!"
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook

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

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

Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

9.8 out of 10, Exceptional, (26)
"Beautiful place, clean , enjoyable beachside"
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage

Southold Cottage w/ Patio & Grill - Walk to Beach!

Southold Cottage w/ Patio & Grill - Walk to Beach!

Cozy Cottage Ponquogue Hampton Bays

2.0 star property
Cozy Cottage Ponquogue Hampton Bays
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 Sag Harbor

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1168)
"excellent overall stay"
The price is CA $208
CA $265 total
includes taxes & fees
May 19 - May 20
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (374)
"Good for a short stay "
The price is CA $227
CA $274 total
includes taxes & fees
May 4 - May 5
Montauk Oceanside Suites
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.