Sag Harbor Vacation Rentals

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Sep 24 - Sep 25
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Vacation Rentals in Sag Harbor

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town
Outdoor dining

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town
Sag Harbor Water View w Dock 1.5ml from town
5 bedrooms, iron/ironing board, WiFi, bed sheets

Sag Harbor Water View w Dock 1.5ml from town

The price is ￥664,245
￥943,736 total
includes taxes & fees
Oct 3 - Oct 4
Sag Harbor Water View w Dock 1.5ml from town
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
Exterior

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

9.0 out of 10, Wonderful, (2)
"Great location and comfortable stay, amazing sheets.Ended up buying for my home. "
Modern Sag Harbor Escape, Moments from the Water and Long Beach to View...
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1250)
"I had the best time and highly recommend this hotel!"
The price is ￥43,840
￥52,977 total
includes taxes & fees
Oct 24 - Oct 25
Montauk Manor
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Living area | TV

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is ￥19,449
￥25,432 total
includes taxes & fees
Oct 19 - Oct 20
Windward Shores Ocean Resort
Montauk Oceanside Suites
Apartment | Private kitchen | Fridge, microwave, stovetop

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (414)
"We loved it, suite size was great! "
The price is ￥20,087
￥24,554 total
includes taxes & fees
Oct 21 - Oct 22
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is ￥46,711
￥59,782 total
includes taxes & fees
Oct 2 - Oct 3
Cliffside Resort Condominiums
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (277)
"Very close walk to the beach great for little ones "
The price is ￥33,045
￥45,781 total
includes taxes & fees
Sep 25 - Sep 26
The Surf Club
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

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

8.8 out of 10, Excellent, (27)
"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
Driftwood Resort
Apartment, 1 Bedroom | Private kitchen | Fridge, microwave, cookware/dishes/utensils

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
The price is ￥20,421
￥28,143 total
includes taxes & fees
Sep 29 - Sep 30
Driftwood Resort
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Outdoor pool, a heated pool

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is ￥25,906
￥59,954 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (31)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Interior

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (74)
"The room was very nicely decorated and clean and had everything you would need. We enjoyed our stay here and appreciated not having to bring linens and towels to a vrbo rental. The only issues we faced not booking directly with the hotel was not being able to use hotel shuttle to town and we ran out of toilet paper and the front desk said they are not supoosed to provide it as we didnt book through them. Other than that the property is very nice providing seating outside to enjoy a beautiful...
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Fairy Tale Guest Cottage in Magic Garden by Pool
Property grounds

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (74)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Outdoor pool, a heated pool

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

10.0 out of 10, Exceptional, (189)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is ￥65,805
￥121,591 total
includes taxes & fees
Oct 2 - Oct 3
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Cozy sun drenched beach cottage private beach, walk to town, hot tub
Property grounds

Cozy sun drenched beach cottage private beach, walk to town, hot tub

10.0 out of 10, Exceptional, (22)
"A very cozy and peaceful escape, loved the hot tub!"
Cozy sun drenched beach cottage private beach, walk to town, hot tub
Offshore Residences
One Bedroom Condo King with Steam Shower | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

Offshore Residences

4.0 star property
The price is ￥78,086
￥106,078 total
includes taxes & fees
Oct 19 - Oct 20
Offshore Residences
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is ￥9,701
￥26,794 total
includes taxes & fees
Oct 7 - Oct 8
The Stern at Soundview · Beach+Ocean+Sunrise
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥29,522
￥49,597 total
includes taxes & fees
Sep 25 - Sep 26
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

10.0 out of 10, Exceptional, (1)
"Great stay. Would stay again. "
Southampton cozy cottage by the beach
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 Sag Harbor Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Highly recommend!"
Christina 1-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Sag Harbor

Find out more about Sag Harbor

Search for holiday rentals in Sag Harbor on Expedia! You can easily find your home rentals, villas, holiday apartments in Sag Harbor using one of the methods below:

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Look no further and take a look at our great range of rental properties in Sag Harbor!

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?

Sag Harbor Water View w Dock 1.5ml from town: Visitors give good reviews to this Sag Harbor vacation home rental, which is located on the waterfront and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 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 balcony, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Sag Harbor?

With 321 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 The Hamptons Beaches and Havens Beach are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Noyac Golf Club and The Style Bar.

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.