Sag Harbor Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Sag Harbor

Exterior
Sag Harbor Village Chic with water views

Holiday Home in Sag Harbor

9.8 out of 10, Exceptional, (8)
"The lilacs were in bloom and we could walk to town for eggs and milk. A relaxing stay in a beautiful town."
United States
Claire W.
Sag Harbor Village Chic with water views
1 bedroom, WiFi, bed sheets
Sag Harbor Suite by the Beach

Apartment in Sag Harbor

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."
United States
Roy L.
Sag Harbor Suite by the Beach
Front of property – evening/night
Montauk Manor

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1262)
"Always excellent, even suring my eleventh stay."
United States
Daryl
The price is HK$1,079
HK$1,385 total
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor
Beach nearby
Cliffside Resort Condominiums

Aparthotel in Greenport

3.0 star property
9.0 out of 10, Wonderful, (248)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Private kitchen
Montauk Oceanside Suites

Aparthotel in Downtown Montauk

3.0 star property
8.6 out of 10, Excellent, (417)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team

Holiday Home in East Hampton

9.8 out of 10, Exceptional, (74)
"We had an incredible stay! The property was as advertised. Very easy in and out and stocked with all the essentials to cook, hangout, use the pool or have a movie night. Our host was very responsive throughout the weekend and gave great recommendations. Highly recommend. "
United States
Henry S.
Stunning Hampton Holiday Family Fantasy for your Team
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Holiday Home in Sag Harbor

10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Private kitchen
Driftwood Resort

Condo in Montauk

3.5 star property
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Holiday Home in Southampton

9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

9.2 out of 10, Wonderful, (36)
"Cottage itself clean, but sewage smell in bathroom. Surrounding property derelict motel with ongoing consruction. "
United States
michelle
The price is HK$560
HK$1,400 total
includes taxes & fees
1 Dec - 2 Dec
1-bedroom cottage with Grove Beach 🏖️ access.
Living area
Offshore Residences

Condo in Downtown Montauk

4.5 star property
The price is HK$3,728
HK$5,149 total
includes taxes & fees
23 Nov - 24 Nov
Offshore Residences
Outdoor pool, a heated pool
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Holiday Home in Hampton Bays

9.4 out of 10, Exceptional, (75)
"Great Hamptons break with family. We had an amazing time with great pool, tennis, firepit and beautiful house. Very relaxing and close to fantastic beaches and nice ice cream spots and beach bars."
United Kingdom
Jack T.
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Holiday Home in Montauk

10.0 out of 10, Exceptional, (61)
"Amazing stay…. Great host, excellent location and very clean!"
Australia
Amy W.
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Outdoor pool, a heated pool
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Holiday Home in Westhampton Beach

10.0 out of 10, Exceptional, (194)
"My family and I thoroughly enjoyed our stay! The house is very spacious and the outdoor area/pool are beautiful. Check-in was a breeze and the host was very friendly and responsive to all our questions about the home as well as offering wonderful suggestions for restaurants and beaches in the area. Would definitely recommend for a family vacation!"
United States
livinann
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Smart TV, fireplace, stereo
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

Holiday Home in East Hampton

10.0 out of 10, Exceptional, (95)
"Awesome location. Very comfortable stay. Had everything we needed. Would definitely stay here again"
United States
Irish T.
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings
Oven, stovetop, dishwasher
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Holiday Home in Calverton

2.0 star property
8.6 out of 10, Excellent, (8)
"This was a great place to stay! Nice house, great backyard on a river and the house was well stocked with essentials. Owner was accommodating and easy to communicate with."
United States
Nicole A.
The price is HK$2,403
HK$5,173 total
includes taxes & fees
23 Nov - 24 Nov
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

Condo in Montauk

9.8 out of 10, Exceptional, (98)
"Very Nice stay there for business would go back for pleasure"
United States
Joseph C.
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
On the beach
The Bridge at Soundview · Beach+OceanView+Sunrise

Apartment in Old Lyme

2.0 star property
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
United States
Emotional J.
The price is HK$993
HK$3,796 total
includes taxes & fees
25 Nov - 26 Nov
The Bridge at Soundview · Beach+OceanView+Sunrise
Terrace/patio
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

Holiday Home in Hampton Bays

9.6 out of 10, Exceptional, (143)
"Large house and deck with plenty of room Beautiful view of bay Not easy to get from deck to water because of boulders "
United States
Robert H.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
On the beach, sun-loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Holiday Home in Montauk

9.8 out of 10, Exceptional, (108)
"Home suited us perfectly for a 10-day vacation with family and friends. The back yard is absolutely fantastic and was perfect for summer grill-outs and pool days. The neighborhood is very quiet and location was spot-on just a 5 minute walk to the beach. Can’t say enough good things about Carter’s home - even better than the pictures!! "
United States
Katie M.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Excellent "
Andrew 1-night trip
Posted 2 days ago
Hyatt Place Long Island East End

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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  • Enter your travel dates to view the best deals on holiday rentals in Sag Harbor while they last

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

Frequently asked questions

Can I find a holiday rental in Sag Harbor?

Yes, there are holiday rentals in Sag Harbor close to Sag Harbor Whaling and Historical Museum, or you can select a more secluded option if you're looking for 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.

How many holiday rentals are there in Sag Harbor?

With 317 Expedia holiday rentals, you're guaranteed to find just the right place for your Sag Harbor stay.

What can I see and do in Sag Harbor?

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

What are holiday rentals like in Sag Harbor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Sag Harbor. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a family getaway.