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Compare 1490 Vacation Homes in Sag Harbor with updated reviews, rates, and availability.

Another rental season is coming up.

10.0 out of 10, Exceptional, (13)
"Ladies weekend. The home was clean and comfortable. We loved how all the kitchen cabinets and drawers were labeled. The host was responsive and accessible The neighborhood was beautiful and close to several of the wineries "
Another rental season is coming up.

Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

10.0 out of 10, Exceptional, (5)
"Our stay at Carters home was nothing short of perfect! Every day we walked to the beach, explored the charming town, grabbed coffee at Hampton Coffee, and enjoyed incredible restaurants nearby. Coming back to such a beautiful and comfortable house felt like a dream. We loved starting our mornings on the patio and cooling off in the pool and eating outside on the big table surrounded by lush flowers—absolute bliss! Highly recommend!""
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

Beautiful Private 4 BR, Heated Pool. Close to Everything.

9.6 out of 10, Exceptional, (42)
"We were in the Hamptons to celebrate my sisters upcoming wedding and had a fantastic time in our rental the only complaint we had was that wish we were there longer!"
Beautiful Private 4 BR, Heated Pool. Close to Everything.

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

9.6 out of 10, Exceptional, (96)
"House was ideal for our extended family for thanksgiving weekend."
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub FREE EV Charger

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

Village Fringe Available May 24th - October 31st. Family/Pet Friendly

10.0 out of 10, Exceptional, (21)
"Very nice home and location, lovely and helpful owner!"
Village Fringe Available May 24th - October 31st. Family/Pet Friendly

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

10.0 out of 10, Exceptional, (13)
"Steps to probably the most beautiful beach in the Hamptons. Thoroughly enjoyed our stay, as did the dogs. We will definitely be back."
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

9.8 out of 10, Exceptional, (98)
"Had a great experience at this property!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

10.0 out of 10, Exceptional, (168)
"We had a wonderful stay. The house was great and check in and check out were both easy. We definition would love to stay again."
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (18)
"My friends and I stayed at this house for a few days around New Year's. The house is very spacious, and the grounds are lovely. We had a group of 5 and had lots of room to congregate and disappear if we needed alone time. The hot tub was exactly what some of us needed, while the kitchen provided others with much comfort. The one bummer was when we arrived; it looked like someone had just had a party outside so that first made for a bit of cleanup. That little bump shouldn't stop you from...
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"The property is located in a discreet area but within easy reach (2miles) of East Hampton. There is a path to a wonderful beach. The hosts were great and provided a useful guide to the area. The house is just right - practical kitchen, clean bathrooms (with bathtub!), cosy rooms. Spacious living room. I liked that the TV room is located downstairs. By the way, the entertainment system is more than sufficient in case bad weather requires time indoors. Their garden is well kept and the outdoors...
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

10.0 out of 10, Exceptional, (47)
"We thoroughly enjoyed staying here, short walk to town, beautiful scenery, quiet and clean. "
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Newly Built 3 Story Home with Beach Parking Pass

9.6 out of 10, Exceptional, (35)
"House was great and spacious, plenty of room and house is laid out nicely with living space on the third story and beds mostly on the second story. Boat was extremely responsive and helpful during the stay. The Location was great, the outdoor deck was nice to spend some time outside and relax after golf. Would definitely come back again. Thank you! "
Newly Built 3 Story Home with Beach Parking Pass

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very Good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court

Beautiful Hamptons home close to beaches, shopping, & restaurants!

10.0 out of 10, Exceptional, (8)
"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "
Beautiful Hamptons home close to beaches, shopping, & restaurants!

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

10.0 out of 10, Exceptional, (5)
"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"
The price is AED 1,837
AED 3,458 total
includes taxes & fees
25 Feb - 26 Feb
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Fall in the🌅beautiful sunsets

10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in the🌅beautiful sunsets

Walk to the beach at Black Point, Niantic, Ct.

9.8 out of 10, Exceptional, (88)
"Beautiful home close to the Sound. Our stay was in February and just happened to coincide with a winter storm. The house was very cozy for my husband and I and our 4 teens. They had a blast watching the LR Roku big screen and eating snacks from the fully equipped kitchen playing ping pong in the downstairs gameroom (note-not really heated in the winter so chilly, but not frigid). Sleeping areas include 2 sofas in downstairs LR, 2 twin beds in upstairs room with fold down desk, 1 full in a cozy...
Walk to the beach at Black Point, Niantic, Ct.

Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

10.0 out of 10, Exceptional, (78)
"We loved our stay in this home! It was the perfect size for our extended family. It was well appointed. The kids loved playing in both levels of the garage. The kitchen had everything we needed. The beds were all comfy. We even took a dip in the cold pool! The owner was responsive to our requests and met all of our needs. I highly recommend this home!"
Westhampton Beach Cedar Shingle with Heated Pool & Gym - on a Private Road

Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!

9.8 out of 10, Exceptional, (7)
"Family friendly, clean and well-stocked house with nice deck and pool for entertaining. It has personality. Well stocked kitchen (note - includes french press and a pod system but you need to bring your own pods; no coffee maker or kettle at time of our stay). Plenty of spices and condiments and entertaining ware as this is also their vacation home. Conveniently located near the highway and walkable to commercial area and 10 min drive to nearest beaches (it does back up to highway so gets road...
Best location! Cozy and Chic Retreat 5 min to beach and close to town, peaceful!
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

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.4 out of 10, Good, (3)
"I had so much fun with my friends"
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1116)
"We loved the manor, it had great amenities and an excellent experience. highly recommend! "
The price is AED 481
AED 621 total
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AED 412
AED 507 total
includes taxes & fees
27 Feb - 28 Feb
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.