Sag Harbor Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday 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
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...
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
Interior

Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum

10.0 out of 10, Exceptional, (50)
"Great house, kitchen is well equipped which made dining in very easy. Loved the pool and backyard."
Heated pool/5 min walk to Beach/Beautiful Sag Harbor Village /Restaurant/Museum
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
3 bedrooms, WiFi, bed sheets

Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi

2.0 star property
7.0 out of 10, Good, (8)
"We had a fantastic stay! The home was exactly as described — clean and very comfortable. The location was perfect. We loved being close to town. Communication was smooth and easy — Frank was quick to respond. We’d absolutely stay here again and recommend it to anyone visiting the area! "
Charming 3-bedroom, 3 bath house in l Sag village, Harbor with pool, AC, WiFi
Luxury Resort-Style Retreat in the Heart of Sag Harbor with Heated Pool,...
Interior

Luxury Resort-Style Retreat in the Heart of Sag Harbor with Heated Pool,...

10.0 out of 10, Exceptional, (1)
"beautiful place"
Luxury Resort-Style Retreat in the Heart of Sag Harbor with Heated Pool,...
Windward Shores Ocean Resort
Living area

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (296)
"Very nice & affordable "
Windward Shores Ocean Resort
Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1252)
"Beautiful grounds, excellent staff"
The price is HK$2,311
HK$2,793 total
includes taxes & fees
24 Oct - 25 Oct
Montauk Manor
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (414)
"We loved it, suite size was great! "
The price is HK$1,059
HK$1,294 total
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (241)
"Great view of the water and nice amenities with the beach and pool."
The price is HK$1,742
HK$2,328 total
includes taxes & fees
2 Nov - 3 Nov
Cliffside Resort Condominiums
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (278)
"Very close walk to the beach great for little ones "
The Surf Club
Driftwood Resort
Private kitchen

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (235)
"Great place to stay for small family "
The price is HK$1,120
HK$1,533 total
includes taxes & fees
13 Oct - 14 Oct
Driftwood Resort
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, (28)
"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
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, (32)
"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
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)
"We had a one-night stay at this location. It was perfect for us from many perspectives and we enjoyed staying there. Very nice place!Thanks! "
The price is HK$1,289
HK$3,055 total
includes taxes & fees
7 Oct - 8 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor
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 HK$1,362
HK$2,344 total
includes taxes & fees
7 Oct - 8 Oct
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
On the beach

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

9.8 out of 10, Exceptional, (96)
"Very Nice stay there for business would go back for pleasure"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
Beach

Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!

2.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed our time in Westbrook! Hosts were more than accomodating and helpful throughout our stay - thank you! House is cute, the perfect size for a small group, and in a good location (walking distance to many shops and restaurants). Private beach access is easy to get to (beach area is small, but it worked!)"
Perfect Shoreline Stay – Walk to Beach, Dine, Shop & Play!
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, (75)
"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
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Interior

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (74)
"We were so excited to come back to this property after our lovely stay in february! We had an amazing time again and loved it! "
MONTAUK MANOR-DELUXE STUDIO APARTMENT
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Terrace/patio

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (137)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sag Harbor Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Fantastic stay. Will return."
Ian 2-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

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:

  • View our selection of featured holiday rentals in Sag Harbor
  • Use the map to find apartments and other holiday homes in the Sag Harbor neighbourhood you prefer
  • 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.

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

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This holiday home rental outside of Sag Harbor offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Sag Harbor?

With 321 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 Havens Beach and Foster Memorial Town 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 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.