A marina with several boats docked, including a white motorboat and a sailboat with a canopy.

Sag Harbor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Sag Harbor vacation rentals

A modern kitchen with a stainless steel refrigerator, white cabinets, a window with a view, and a chandelier.

1. Charming Accommodations in the Hamptons

Charming Accommodations in the Hamptons
Sag Harbor
The price is ￥38,776
￥84,807 total
includes taxes & fees
Sep 28 - Sep 29
Charming Accommodations in the Hamptons
A backyard with a swimming pool, wicker lounge chairs, and potted plants.

2. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
10.0 out of 10, Exceptional, (1 review)
"excellent and convenient stay!! located close into town, perfect for the small family group I was traveling with. home was very clean, cozy, had everything we needed! backyard with pool was a dream, beautifully landscaped, plenty of seating, very clean pool, would stay again! thanks for a delightful escape!"
United States
maria m.
The price is ￥89,739
￥176,305 total
includes taxes & fees
Sep 28 - Sep 29
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
A compact laundry room with a washing machine, a dryer, and a small sink area.

3. Lovely & Spacious Sag Harbor escape with heated pool

Lovely & Spacious Sag Harbor escape with heated pool
Sag Harbor
The price is ￥242,153
￥336,332 total
includes taxes & fees
Sep 26 - Sep 27
Lovely & Spacious Sag Harbor escape with heated pool
A modern kitchen with a black and white color scheme, a central island, and built-in appliances.

4. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
Sag Harbor
The price is ￥296,598
￥404,141 total
includes taxes & fees
Sep 29 - Sep 30
Spacious & Modern 5-bedroom in Sag Harbor, walk to bay
A small cabin with a porch, surrounded by trees and a fenced area.

5. Lovely studio with AC in charming Sag Harbor

Lovely studio with AC in charming Sag Harbor
Sag Harbor
6.0 out of 10, (1 review)
"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...
United States
Emily t.
The price is ￥38,776
￥86,798 total
includes taxes & fees
Sep 27 - Sep 28
Lovely studio with AC in charming Sag Harbor
A campsite with several tents and a picnic table.

6. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is ￥34,015
￥51,523 total
includes taxes & fees
Oct 1 - Oct 2
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
A tented accommodation with two beds, a small table, a chair, and a cabinet.

7. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

Safari Tent Glamping,D27-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (5 reviews)
"We loved the idea of "roughing it" while still sleeping in a cozy bed. It was nice to expose my children to nature. We took a long walk on the beach. Cooked hotdogs and hamburgers on the grill and made s'mores on the campfire."
United States
Brian
The price is ￥30,707
￥49,232 total
includes taxes & fees
Sep 27 - Sep 28
Safari Tent Glamping,D27-CedarPt, East Hampton, NY
A campsite with several tents set up among trees.

8. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

Safari Tent Glamping,D28-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (5 reviews)
"It was a really great experience! We barbecued and made a camp fire. Took a walk on the beach. Played in the playground. The pizza and breakfast sandwiches in the café were delicious! We will definitely be coming back!"
United States
Brian F.
The price is ￥34,015
￥53,511 total
includes taxes & fees
Oct 1 - Oct 2
Safari Tent Glamping,D28-CedarPt, East Hampton, NY

9. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (2 reviews)
"Absolutely Beautiful view The vibe and food was great. Just beware of the tics."
United States
Christina V.
The price is ￥34,015
￥51,523 total
includes taxes & fees
Oct 1 - Oct 2
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

10. Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (323 reviews)
"Easy access to the beach. Perfect weather. Nicely furnished and updated rooms and bathrooms. The gym is tiny- not much equipment. The location is perfect for Montauk and Amagansett. The staff were very nice and hard working."
United States
Gaurang J
The price is ￥18,826
￥25,812 total
includes taxes & fees
Oct 12 - Oct 13
Windward Shores Ocean Resort
A modern house with a deck, outdoor seating, and a fire pit.

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (58 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥40,886
￥46,711 total
includes taxes & fees
Oct 25 - Oct 26
North Fork Resort
A spacious hallway with high ceilings, arched columns, and chandeliers.

12. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,407 reviews)
"Excellent service, beautiful property, accommodating staff."
United States
Maria
The price is ￥20,417
￥26,425 total
includes taxes & fees
Oct 12 - Oct 13
Montauk Manor
A dining area with a round table, six chairs, and a chandelier.

13. Year round Jacuzzi - Blackberry Home

Year round Jacuzzi - Blackberry Home
East Hampton
9.2 out of 10, Wonderful, (7 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is ￥17,939
￥209,804 total
includes taxes & fees
Sep 27 - Sep 28
Year round Jacuzzi - Blackberry Home
A spacious living room with a high ceiling, a fireplace, and a staircase leading to an upper level.

14. East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace

East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
East Hampton North
10.0 out of 10, Exceptional, (3 reviews)
"This house is absolutely wonderful and in a great location. It is beautifully decorated and the grounds are immaculate. The host has paid close attention to detail; everything we could ever need was there! We loved our stay, highly highly recommend ....."
United States
Carolyn C.
East Hampton Estate for 10, Pool Open through October, Sauna, Chef`s Kitchen, Outdoor Fireplace
A spacious living area with a large bed, a dining table, and a kitchen in the background.

15. Unit 1021: Studio | 2nd Floor-Pool View | Starfish

Unit 1021: Studio | 2nd Floor-Pool View | Starfish
Napeague
9.8 out of 10, Exceptional, (6 reviews)
"Comfortable accommodations, easy access to pool and beach, close to restaurants, quiet."
United States
Liana T.
The price is ￥25,640
￥66,532 total
includes taxes & fees
Sep 28 - Sep 29
Unit 1021: Studio | 2nd Floor-Pool View | Starfish

16. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (294 reviews)
"Great place!"
United States
Christine
The price is ￥43,861
￥67,725 total
includes taxes & fees
Oct 25 - Oct 26
Cliffside Resort Condominiums

17. Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
8.8 out of 10, Excellent, (251 reviews)
"Best value and bang for your buck in Montauk other than Wavecrest in Amagansett."
United States
William
The price is ￥25,891
￥34,736 total
includes taxes & fees
Oct 4 - Oct 5
Driftwood Resort

18. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (452 reviews)
"The room was very clean and spacious."
United States
Jadana
The price is ￥18,695
￥23,082 total
includes taxes & fees
Oct 20 - Oct 21
Montauk Oceanside Suites
A beach with people relaxing on chairs and sunbathing.

19. Harbor Heights

Harbor Heights
Pipes Cove
10.0 out of 10, Exceptional, (26 reviews)
"Perfect spot to stay on the North Fork!"
United States
Steven R.
The price is ￥20,654
￥45,840 total
includes taxes & fees
Oct 5 - Oct 6
Harbor Heights
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
"The person checking us in was very pleasant and helpful. The rooms were clean and well kept, noise level was low and not disturbing. Price was very reasonable."
Steven 1-night trip
Posted 5 hours ago
Pier Blue Inn Old Saybrook - Essex

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:

  • View our selection of featured holiday rentals in Sag Harbor
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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 Bay Street Theatre, 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?

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly: Located near Sag Harbor, this vacation home rental offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Sag Harbor?

With 312 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 Elizabeth A. Morton National Wildlife Refuge.

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.