Sag Harbor Vacation Rentals

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Our top choices for Sag Harbor vacation rentals

Sag Harbor Water View w Dock 1.5ml from town

Sag Harbor Water View w Dock 1.5ml from town
Bay Point
The price is CA $2,452
CA $3,798 total
includes taxes & fees
Apr 30 - May 1
Sag Harbor Water View w Dock 1.5ml from town

Spacious 5-bedroom house with water views and 2 houses from the bay.

Spacious 5-bedroom house with water views and 2 houses from the bay.
Sag Harbor
The price is CA $5,450
CA $8,751 total
includes taxes & fees
May 2 - May 3
Spacious 5-bedroom house with water views and 2 houses from the bay.

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is CA $342
CA $551 total
includes taxes & fees
May 25 - May 26
Floating Nest on Private River. Serene Views & Ultimate Relaxation

Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S5-CedarPt, East Hampton, NY
East Hampton
8.6 out of 10, Excellent, (4 reviews)
"We loved our tent, the view was great. The bed was super comfortable. We will definitely come back and hopefully stay longer. Also, the pizza is so good as was the watermelon Margherita."
United States
Jennifer
The price is CA $293
CA $439 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,S5-CedarPt, East Hampton, NY

Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Safari Tent Glamping,S6-CedarPt, East Hampton, NY
East Hampton
9.0 out of 10, Wonderful, (4 reviews)
"We loved the surroundings, the pizza restaurant with live music and ping pong, and the friendly, warm atmosphere and kind staff. We do wish the bathrooms and especially the showers were cleaner."
United States
Lorraine
The price is CA $293
CA $439 total
includes taxes & fees
May 21 - May 22
Safari Tent Glamping,S6-CedarPt, East Hampton, NY

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,333 reviews)
"Incredible place to stay "
United States
melissa
The price is CA $206
CA $262 total
includes taxes & fees
May 12 - May 13
Montauk Manor

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is CA $109
CA $246 total
includes taxes & fees
Apr 29 - Apr 30
1-bedroom cottage with Grove Beach 🏖️ access.

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is CA $254
CA $290 total
includes taxes & fees
May 6 - May 7
North Fork Cottages & RV Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $196
CA $283 total
includes taxes & fees
Apr 29 - Apr 30
Cliffside Resort Condominiums

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (311 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is CA $217
CA $285 total
includes taxes & fees
May 4 - May 5
Windward Shores Ocean Resort

The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very good, (2 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is CA $155
CA $330 total
includes taxes & fees
Apr 29 - Apr 30
The Anchor at Soundview · Beach+Ocean+Sunrise

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (423 reviews)
"Clean. Great location to beach and town."
United States
Cheryl
The price is CA $168
CA $207 total
includes taxes & fees
Apr 29 - Apr 30
Montauk Oceanside Suites

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (55 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is CA $153
CA $371 total
includes taxes & fees
May 10 - May 11
Insta-worthy Couples Retreat: Perfect for romantic getaway!

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is CA $293
CA $439 total
includes taxes & fees
May 28 - May 29
Safari Tent Glamping,S10-CedarPt, East Hampton, NY

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (236 reviews)
"Great place to stay for small family "
United States
DongHo
The price is CA $212
CA $287 total
includes taxes & fees
May 17 - May 18
Driftwood Resort

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (280 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is CA $228
CA $335 total
includes taxes & fees
May 12 - May 13
The Surf Club

American Beech in Greenport - Petite King Room 7

American Beech in Greenport - Petite King Room 7
Greenport
9.2 out of 10, Wonderful, (5 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is CA $230
CA $361 total
includes taxes & fees
Apr 29 - Apr 30
American Beech in Greenport - Petite King Room 7

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"This is a must property for any vacationer traveling to Long Island. You will fall in love with quiet evenings after delightful beach walks. Don’t forget the therapeutic ocean air! Within very short walking distance, you are near The Pavilion and the famous Kokomo’s Restaurant. Kokomo’s is the best ocean restaurant in Old Lyme for a reason, with fantastic ocean views and an unmatched family dining experience. As Old Lyme begins its long-awaited restoration project, this beach apartment will...
United States
Jennivere
The price is CA $203
CA $392 total
includes taxes & fees
Apr 30 - May 1
Keel at Soundview · Beach+OceanView+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is CA $162
CA $338 total
includes taxes & fees
Apr 29 - Apr 30
Freeboard at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is CA $162
CA $338 total
includes taxes & fees
Apr 29 - Apr 30
The Stern at Soundview · Beach+Ocean+Sunrise
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

Find out more about Sag Harbor

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 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?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home near Sag Harbor offers an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Sag Harbor?

With 313 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 Foster Memorial Town Beach.

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.