Sag Harbor Vacation Rentals

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Vacation Rentals in Sag Harbor

Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
1 bedroom, WiFi, bed sheets
Sag Harbor Suite by the Beach
9.0 out of 10, Wonderful, (8)
"We were in town to celebrate thanksgiving. Nice cozy 1 bedroom apartment. 5 minute drive to town."
Sag Harbor Suite by the Beach
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1019)
"Best affordable hotel in Montauk"
The price is CA $229
CA $288 total
includes taxes & fees
May 20 - May 21
Montauk Manor
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Apartment | Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (295)
"We enjoyed our stay!"
The price is CA $223
CA $269 total
includes taxes & fees
May 30 - May 31
Montauk Oceanside Suites
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"An amazing stay with our girls!!! Can’t wait to go back!"
The price is CA $306
CA $423 total
includes taxes & fees
May 29 - May 30
The Surf Club
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (235)
"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"
The price is CA $210
CA $269 total
includes taxes & fees
May 16 - May 17
Windward Shores Ocean Resort
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (181)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is CA $336
CA $443 total
includes taxes & fees
May 16 - May 17
Cliffside Resort Condominiums
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (184)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is CA $222
CA $283 total
includes taxes & fees
Jun 2 - Jun 3
Driftwood Resort
Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
Beach nearby, sun loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (60)
"Perfect spot in Montauk, close to the beach and town. We walked to town with a 3 year old and infant in the stroller and very doable nice walk. The condo is clean and equipped with basic necessities so bring anything you might need cooking wise. Kept the baby in the bedroom and our 3 year old in the living room but we made it work. Kelly is extremely responsive and a pleasure to rent from."
Newly Renovated Montauk Condo with Ocean Views!
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
Microwave, oven, stovetop, coffee/tea maker
Contemporary home, newly built, heated pool and hot tub, large deck and...
10.0 out of 10, Exceptional, (4)
"The property manager was incredibly helpful in providing check-in and check-out information, and was readily available to answer any questions during our stay. The house perfectly matched what we saw in the photos and was ideal for our getaway. We're already looking forward to returning in the summertime to fully enjoy the pool."
Contemporary home, newly built, heated pool and hot tub, large deck and...
On the beach, sun loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (89)
"We unfortunately had bad weather during our stay but we were cozy in this home which is spacious and conveniently located. For those with kids, there are safety gates and toys available. There’s a lot of outdoor seating and in the summer we look forward to returning to take advantage of the pool. Carter is very responsive - a terrific host!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (71)
"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Outdoor dining
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
10.0 out of 10, Exceptional, (83)
"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"
The price is CA $887
CA $1,326 total
includes taxes & fees
May 20 - May 21
Beachy Chic South of the Hwy in Southampton Village 3blks to town/Bike to 🏖
Sun loungers, beach towels
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
10.0 out of 10, Exceptional, (145)
"We had an amazing time at Mark's house. The home is clean and well maintained with many amenities that made the weekend extra special (cool nights by the fire pit were especially awesome)! Mark gave detailed directions about the house and provided us with lots of information about the neighborhood. Plenty of space for all 12 of us to be together. Highly recommend this rental!"
The price is CA $676
CA $1,076 total
includes taxes & fees
May 29 - May 30
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Lobby
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
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See all available properties in Sag Harbor
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.

Other types of properties in Sag Harbor you may be interested in

Outdoor pool
Sag Harbor Inn
3.5 star property
9.4 out of 10, Exceptional, (422)
"I stay here often. Reliable and consistent hotel. Rooms are spotless. Perfect for single or retired traveler. It’s quiet and attracts a middle aged crowd. Walking distance to town. I’ve never had an issue."
The price is CA $319
CA $365 total
includes taxes & fees
May 16 - May 17
Sag Harbor Inn
Front of property - evening/night
Baron's Cove
3.5 star property
9.0 out of 10, Wonderful, (133)
"We loved everything about our stay - the location, the cleanliness, the service, Kristen at the front desk :-), the food (we had breakfast and brunch at the hotel during our two days there) - can't wait to go back to Baron's Cove!!!!"
The price is CA $449
CA $564 total
includes taxes & fees
May 29 - May 30
Baron's Cove
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Sag Harbor. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.

How many vacation rentals are there in Sag Harbor?

With 338 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 Sag Harbor Marine Park and The Hamptons Beaches are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Beach Bungalow and Noyac Golf Club.

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.

Recent reviews of Sag Harbor properties
Expedia verified reviews