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Holiday Rentals in Shelter Island Heights

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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 Shelter Island Heights

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 €155
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor
Free WiFi, bed sheets
North Fork Cottages & RV Resort

Cottage in Greenport

3.0 star property
9.4 out of 10, Exceptional, (6)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is €174
includes taxes & fees
24 Nov - 25 Nov
North Fork Cottages & RV Resort
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Holiday Home in Water Mill

10.0 out of 10, Exceptional, (6)
"Highly recommend everything from start to finish went smoothly and it was a great experience!!"
United States
Stephanie M.
The price is €6,485
includes taxes & fees
1 Dec - 2 Dec
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Holiday Home in Old Lyme

10.0 out of 10, Exceptional, (3)
"We were very comfortable during our stay. The amenities at the house and in the vicinity were great. Our hosts were very responsive in answering our questions. We watched the World Series on the large screen TV in the den. All the family members we had stay with us during the week had ample space to sleep and stretch out. We loved the Yoga studio too. Many thanks!"
United States
Nicole B.
The price is €359
includes taxes & fees
24 Nov - 25 Nov
Rogers Lake House (87) · CT College+Beach+USCGA
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Mobile Home in East Lyme

10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is €179
includes taxes & fees
24 Nov - 25 Nov
Lakefront Boho Tiny House
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

2.0 star property
8.0 out of 10, Very good, (2)
"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 €172
includes taxes & fees
24 Nov - 25 Nov
The Anchor at Soundview · Beach+Ocean+Sunrise
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

10.0 out of 10, Exceptional, (1)
The price is €405
includes taxes & fees
25 Nov - 26 Nov
Seabreeze #3: Cozy Cottage by the beach
Fridge, microwave, oven, stovetop
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Holiday Home in Waterford

10.0 out of 10, Exceptional, (10)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is €321
includes taxes & fees
1 Dec - 2 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Exterior
Cozy Lakefront Tiny House

Mobile Home in East Lyme

10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is €182
includes taxes & fees
24 Nov - 25 Nov
Cozy Lakefront Tiny House
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

2.0 star property
10.0 out of 10, Exceptional, (13)
"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.
The price is €276
includes taxes & fees
24 Nov - 25 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Beach
Spacious 5-bedroom house with water views and 2 houses from the bay.

Holiday Home in Sag Harbor

The price is €5,713
includes taxes & fees
27 Nov - 28 Nov
Spacious 5-bedroom house with water views and 2 houses from the bay.
5 bedrooms, iron/ironing board, WiFi, bed sheets
Sag Harbor Water View w Dock 1.5ml from town

Holiday Home in Bay Point

The price is €5,690
includes taxes & fees
25 Nov - 26 Nov
Sag Harbor Water View w Dock 1.5ml from town
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 €160
includes taxes & fees
1 Dec - 2 Dec
1-bedroom cottage with Grove Beach 🏖️ access.
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Holiday Home in East Hampton

9.0 out of 10, Wonderful, (4)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
United States
Suzanne R.
The price is €762
includes taxes & fees
24 Nov - 25 Nov
Blackberry: Private home with jacuzzi year-round
Beach nearby
Insta-worthy Couples Retreat: Perfect for romantic getaway!

Holiday Home in Old Lyme

9.6 out of 10, Exceptional, (52)
"Great stay, charming cottage, hope to return"
United States
Ellen C.
The price is €224
includes taxes & fees
30 Nov - 1 Dec
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Front of property
Canoe Place Waterfront Residences

Condo in Hampton Bays

4.0 star property
10.0 out of 10, Exceptional, (1)
The price is €1,784
includes taxes & fees
22 Dec - 23 Dec
Canoe Place Waterfront Residences
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Holiday Home in Hampton Bays

10.0 out of 10, Exceptional, (12)
"This is a simple house with a great view right on the water. The beds and bedding were comfortable. Despite being on the water, it has a nice yard and little beach area. "
United States
Coleman H.
The price is €1,104
includes taxes & fees
10 Dec - 11 Dec
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Holiday Home in Hampon Bays

9.6 out of 10, Exceptional, (22)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is €1,132
includes taxes & fees
1 Dec - 2 Dec
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Fridge, microwave, oven, stovetop
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Cottage in Old Saybrook Center

9.6 out of 10, Exceptional, (38)
"Great property, would stay here again."
United States
charles b.
The price is €453
includes taxes & fees
24 Nov - 25 Nov
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Private kitchen
Stylish Modern Stay Steps from the Ocean

Holiday Home in Clinton

10.0 out of 10, Exceptional, (1)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is €270
includes taxes & fees
29 Nov - 30 Nov
Stylish Modern Stay Steps from the Ocean
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 Heights Hotel Reviews

Best Western Niantic - New London/Mystic Area

Best Western Niantic - New London/Mystic Area

10/10 Excellent
"Very clean room and the maid was super helpful! She helped me find scissors for these impossible hair ties in my daughter’s hair. The breakfast was great! Gravy and biscuits? Heck ya! "
Vickie 1-night trip
Posted 2 days ago
Best Western Niantic - New London/Mystic Area

Find out more about Shelter Island Heights

Everything you need to know about Shelter Island Heights holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island Heights holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Heights holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shelter Island Heights holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island Heights holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island Heights holiday rentals we have selected for you start as low as €155 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shelter Island Heights rentals

At Expedia, we put the best Shelter Island Heights holiday 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 Heights 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 Heights holiday.

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 Heights. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Shelter Island Heights?

Yes, there are holiday rentals close to the most popular sights in Shelter Island Heights, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the beaches in Shelter Island Heights. Make sure you have time to check out the golf courses and entertainment choices during your trip.

How many holiday rentals are there in Shelter Island Heights?

With 33 Expedia holiday rentals, you're guaranteed to find just the right place for your Shelter Island Heights stay.

What’s there to see and do in Shelter Island Heights?

Sunset Beach and Crescent Beach are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Shelter Island Country Club and Sylvester Manor.

What’s a holiday rental in Shelter Island Heights like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Shelter Island Heights. Holiday rentals feature extras such as patios, hot tubs and fire pits so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.