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Shelter Island Vacation Rentals

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Vacation Rentals in Shelter Island

Property grounds
Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount

Shelter Island
10.0 out of 10, Exceptional, (52)
"The house was amazing ,clean and full of good energy.it had everything we needed for peaceful, relaxing getaway serenity now! "
United States
moshe A.
$1,165 nightly
The price is $1,331
Nov 11 - Nov 12
Total with taxes and fees
Work and Play Special! Extended Stay Discount
Interior
Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Old Lyme
$330 nightly
The price is $374
Nov 11 - Nov 12
Total with taxes and fees
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Free WiFi, bed sheets
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
10.0 out of 10, Exceptional, (1)
"Great stay! Very clean and new. Comfy beds, great location "
United States
Lisa
$195 nightly
The price is $223
Nov 13 - Nov 14
Total with taxes and fees
North Fork Cottages & RV Resort
Front of property - evening/night
Montauk Manor

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1260)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
$156 nightly
The price is $178
Dec 1 - Dec 2
Total with taxes and fees
Montauk Manor
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
$171 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA

Old Lyme
10.0 out of 10, Exceptional, (3)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
$356 nightly
The price is $403
Nov 10 - Nov 11
Total with taxes and fees
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV
Hidden gem! Southampton beach cottage

Hidden gem! Southampton beach cottage

Hampton Bays
10.0 out of 10, Exceptional, (1)
$394 nightly
The price is $450
Nov 16 - Nov 17
Total with taxes and fees
Hidden gem! Southampton beach cottage
Exterior
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Waterford
10.0 out of 10, Exceptional, (10)
"Open concept home beautiful with private yard space. It was perfect for our stay"
United States
Berlyne S.
$319 nightly
The price is $361
Nov 17 - Nov 18
Total with taxes and fees
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
Waterford
10.0 out of 10, Exceptional, (12)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
$275 nightly
The price is $311
Nov 10 - Nov 11
Total with taxes and fees
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
$192 nightly
The price is $218
Nov 11 - Nov 12
Total with taxes and fees
1-bedroom cottage with Grove Beach 🏖️ access.
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Water Mill
10.0 out of 10, Exceptional, (6)
"Our family / extended family was in town for over a week for the Hampton Classic horse show. We all enjoyed or stay at this wonderful home: beautiful newly renovated open space, outstanding kitchens (indoors and outdoors), numerous areas to have separate down time, excellent in suite bedroom / bathrooms including three bedrooms suites with king beds, fabulous backyard with a private pool, and exceptionally clean with all amenities needed. The owners were also incredible; extremely responsive,...
United States
Kristin C.
$4,797 nightly
The price is $5,481
Nov 10 - Nov 11
Total with taxes and fees
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Fridge, microwave, oven, stovetop
Cozy quiet gem, private & fenced in backyard

Cozy quiet gem, private & fenced in backyard

East Hampton
9.4 out of 10, Exceptional, (3)
"Just hubby & I. Great fireplace and deck with very clean bubbly hot tub. Comfy king-sized bed. Kitchen was clean & functional with basics. Backyard appeared larger in pictures. Rental could use extra couch in living room to comfortably fit eight ppl. The living room couch is just for sitting, appears larger in pictures. Couch is"
United States
STEPHANIE C.
$771 nightly
The price is $881
Nov 10 - Nov 11
Total with taxes and fees
Cozy quiet gem, private & fenced in backyard
Terrace/patio
Year-Round Private Jacuzzi / Peaceful Fenced Yard

Year-Round Private Jacuzzi / Peaceful Fenced Yard

Hampon Bays
9.6 out of 10, Exceptional, (22)
"What a great place for a family gathering! The backyard is to die for and the host was very helpful throughout the stay. We’ll be back!!"
United States
Lisa w.
$1,113 nightly
The price is $1,272
Nov 16 - Nov 17
Total with taxes and fees
Year-Round Private Jacuzzi / Peaceful Fenced Yard
Front of property
Canoe Place Waterfront Residences

Canoe Place Waterfront Residences

4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1)
$2,115 nightly
The price is $2,416
Nov 23 - Nov 24
Total with taxes and fees
Canoe Place Waterfront Residences
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Old Lyme
9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
$234 nightly
The price is $265
Nov 30 - Dec 1
Total with taxes and fees
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green

2.0 star property
Westbrook
$406 nightly
The price is $459
Nov 11 - Nov 12
Total with taxes and fees
Beachside Bliss w/ Game Room, Gym & Golf Green
Terrace/patio
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

Greenport
10.0 out of 10, Exceptional, (1)
"Wonderful house. Immaculate with all the provisions you can hope for. Perfect location and beautifully done!"
United States
Jeannette M.
$486 nightly
The price is $555
Nov 12 - Nov 13
Total with taxes and fees
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Terrace/patio
Private beach on a fenced in property sunset views

Private beach on a fenced in property sunset views

Hampton Bays
10.0 out of 10, Exceptional, (12)
"Beautiful sunrise, sunsets and scenery. Beautiful property"
United States
Elaine P.
$1,170 nightly
The price is $1,337
Nov 10 - Nov 11
Total with taxes and fees
Private beach on a fenced in property sunset views
Fridge, microwave, oven, stovetop
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Old Saybrook Center
9.6 out of 10, Exceptional, (38)
"Nicely decorated and clean. "
United States
Lauren
$450 nightly
The price is $509
Nov 10 - Nov 11
Total with taxes and fees
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
On the beach
Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
9.6 out of 10, Exceptional, (7)
"It was very close to the beach , quiet, parking on property room had everything you would need i enjoyed my stay didnt want to leave so soon wouldve liked at least 1 more day maybe next year thank you. "
United States
Dana
$172 nightly
The price is $194
Nov 11 - Nov 12
Total with taxes and fees
Freeboard 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 Shelter Island Hotel Reviews

Sag Harbor Inn

Sag Harbor Inn

10/10 Excellent
"Walk into town, right on the water, clean room, watch the sunset and sunrise, beautiful breakfast offerings- what more can you ask for!!"
GINA 1-night trip
Posted 2 days ago
Sag Harbor Inn

Find out more about Shelter Island

Everything you need to know about Shelter Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Shelter Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $178 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation home rentals that Shelter Island has to offer?

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available : This vacation home rental near Shelter Island is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 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 patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island?

Choose from 85 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.