Sag Harbor Vacation Rentals

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Vacation Rentals 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

Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...

8.0 out of 10, Very Good, (1)
"It was nice"
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1195)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is ¥52,991
¥63,390 total
includes taxes & fees
Jun 22 - Jun 23
Montauk Manor

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (285)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is ¥39,202
¥47,952 total
includes taxes & fees
Jun 22 - Jun 23
Windward Shores Ocean Resort

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (381)
"great place to stay"
The price is ¥27,202
¥32,660 total
includes taxes & fees
Jun 23 - Jun 24
Montauk Oceanside Suites

Offshore Montauk

4.0 star property
The price is ¥32,303
¥53,516 total
includes taxes & fees
Jun 24 - Jun 25
Offshore Montauk

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (223)
"The staff was very friendly I will definitely be back again 👍"
The price is ¥46,879
¥58,297 total
includes taxes & fees
Jun 22 - Jun 23
Driftwood Resort

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (256)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is ¥32,546
¥45,090 total
includes taxes & fees
Jun 24 - Jun 25
The Surf Club

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (221)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is ¥36,653
¥48,194 total
includes taxes & fees
Jun 26 - Jun 27
Cliffside Resort Condominiums

3-bedroom Montauk Coastal Getaway

3-bedroom Montauk Coastal Getaway

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Canoe Place Waterfront Residences

4.0 star property
The price is ¥249,429
¥302,070 total
includes taxes & fees
Jun 26 - Jun 27
Canoe Place Waterfront Residences

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (66)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Charming Montauk Getaway centrally located

9.6 out of 10, Exceptional, (43)
"Quiet, private, well-appointed spot with everything you need for a getaway. Conveniently located within walking distance to town, it has its own outdoor area perfect for lounging and cooking out. We loved it!"
Charming Montauk Getaway centrally located

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
The price is ¥10,492
¥27,610 total
includes taxes & fees
Jun 19 - Jun 20
Freeboard at Soundview · Beach+Ocean+Sunrise

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

10.0 out of 10, Exceptional, (85)
"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

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (181)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

10.0 out of 10, Exceptional, (83)
"Great time"
Perfect East Hampton Getaway!Pool, HotTub, PirateShip, Trampoline, Walk to Beach

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

10.0 out of 10, Exceptional, (7)
"We thoroughly enjoyed the home, and Carter was extremely helpful throughout our stay. The private parking access to the beach was awesome!"
Walk 2 Beach; Pool, Hot Tub, Fire Pit in Hither Hills; Private Setting, Sleep 10

Driftwood Cottage by RoveTravel| 3BR Quiet Cottage

9.4 out of 10, Exceptional, (10)
"I stayed here with family recently and loved the house. The location was private and convenient. The management company was available to answer our questions. It was perfect for an off season get away. "
Driftwood Cottage by RoveTravel| 3BR Quiet Cottage
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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Frequently asked questions

Can I find a vacation rental in Sag Harbor?

Yes, we give you a choice of vacation rentals in Sag Harbor close to Sag Harbor Whaling and Historical Museum, or you can go with a more secluded option if you want a relaxing stay. Discover why Sag Harbor is known for its waterfront. Make sure you have time to check out the beaches and churches during your trip.

What are some of the best vacation home rentals that Sag Harbor has to offer?

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub: Visitors give good reviews to this Sag Harbor vacation home rental, which is located by the ocean and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Sag Harbor?

With 334 Expedia vacation rentals, you're sure to find just the right place for your Sag Harbor stay.

What can I see and do in Sag Harbor?

Cultural attractions include Bay Street Theatre and Sag Harbor Whaling and Historical Museum, whereas Havens Beach and The Hamptons Beaches are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Noyac Golf Club and Foster Memorial Town Beach.

What are vacation rentals like in Sag Harbor?

Vacation rentals are private properties you can book for several days or longer in Sag Harbor. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for families.