Photo by Erisa Dilo

Shelter Island Heights Vacation Rentals

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Shelter Island Heights vacation rentals

Front of property - evening/night
Montauk Manor

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1273)
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is ￥21,641
￥27,780 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Montauk Manor
On the beach
The Stern at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Stern at Soundview · Beach+Ocean+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is ￥11,873
￥30,190 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Stern at Soundview · Beach+Ocean+Sunrise
Outdoor pool, a heated pool
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach

Vacation Home in Water Mill

NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
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 ￥656,373
￥1,157,219 total
includes taxes & fees
Jan 5 - Jan 6, 2026
NEW Luxury 7BR Water Mill Estate – Salt Pool, Sauna & Cold Plunge, Mins to Beach
Smart TV
Seabreeze #3: Cozy Cottage by the beach

Cottage in Hampton Bays

Seabreeze #3: Cozy Cottage by the beach
10.0 out of 10, Exceptional, (1)
The price is ￥8,588
￥69,750 total
includes taxes & fees
Jan 27 - Jan 28, 2026
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

Vacation Home in Waterford

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (11)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ￥15,536
￥57,525 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
1 bedroom, free WiFi, bed sheets
Lakefront Boho Tiny House

Mobile Home in East Lyme

Lakefront Boho Tiny House
10.0 out of 10, Exceptional, (3)
"this place was amazing i would come again"
United States
Tatyanna R.
The price is ￥15,845
￥35,484 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Lakefront Boho Tiny House
Exterior
Cozy Lakefront Tiny House

Mobile Home in East Lyme

Cozy Lakefront Tiny House
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 ￥15,673
￥35,130 total
includes taxes & fees
Dec 30 - Dec 31
Cozy Lakefront Tiny House
Property grounds
Rogers Lake House (87) · CT College+Beach+USCGA

Vacation Home in Old Lyme

Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (5)
"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.
The price is ￥13,520
￥63,045 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Rogers Lake House (87) · CT College+Beach+USCGA
Smart TV
1-bedroom cottage with Grove Beach 🏖️ access.

Cottage in Clinton

1-bedroom cottage with Grove Beach 🏖️ access.
9.2 out of 10, Wonderful, (36)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥11,555
￥27,043 total
includes taxes & fees
Dec 28 - Dec 29
1-bedroom cottage with Grove Beach 🏖️ access.
Fridge, microwave, oven, stovetop
The Bay Cottage · Rocky Neck Park, Beach & Niantic

Vacation Home in East Lyme

The Bay Cottage · Rocky Neck Park, Beach & Niantic
2.0 star property
9.0 out of 10, Wonderful, (4)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is ￥18,311
￥57,002 total
includes taxes & fees
Jan 27 - Jan 28, 2026
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Outdoor dining
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cottage in Waterford

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
2.0 star property
10.0 out of 10, Exceptional, (14)
"Cottage was perfect. Immaculate, well equipped, beautifully decorated. It had everything we needed! My family and I loved our stay here and will definitely be back."
United States
Nina B.
The price is ￥23,486
￥50,651 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
On the beach
The Anchor at Soundview · Beach+Ocean+Sunrise

Apartment in Old Lyme

The Anchor at Soundview · Beach+Ocean+Sunrise
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 ￥11,906
￥30,273 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Anchor at Soundview · Beach+Ocean+Sunrise
Terrace/patio
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer

Vacation Home in Hampon Bays

Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
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 ￥15,458
￥198,548 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
Beach
Beachside Bliss w/ Game Room, Gym & Golf Green

Vacation Home in Westbrook

Beachside Bliss w/ Game Room, Gym & Golf Green
2.0 star property
10.0 out of 10, Exceptional, (1)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥21,356
￥78,615 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beachside Bliss w/ Game Room, Gym & Golf Green
Fridge, microwave, oven, stovetop
Blackberry: Private home with jacuzzi year-round

Vacation Home in East Hampton

Blackberry: Private home with jacuzzi year-round
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 ￥15,458
￥142,536 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Blackberry: Private home with jacuzzi year-round
Exterior
Shoreline Oasis

Apartment in Clinton

Shoreline Oasis
9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is ￥28,026
￥40,646 total
includes taxes & fees
Dec 28 - Dec 29
Shoreline Oasis
Terrace/patio
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Vacation Home in Hampton Bays

Black Swan: Beachfront Home w/ Year-Round Jacuzzi
9.6 out of 10, Exceptional, (14)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is ￥23,421
￥198,729 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Black Swan: Beachfront Home w/ Year-Round Jacuzzi
Fridge, microwave, oven, stovetop
Adorable Cottage, 5 min walk to water & town

Vacation Home in Westbrook Center

Adorable Cottage, 5 min walk to water & town
9.4 out of 10, Exceptional, (15)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥27,218
￥65,355 total
includes taxes & fees
Dec 28 - Dec 29
Adorable Cottage, 5 min walk to water & town
Beach
Seabreeze #4: Charming Cottage Footsteps to the Beach

Cottage in Hampton Bays

Seabreeze #4: Charming Cottage Footsteps to the Beach
8.8 out of 10, Excellent, (3)
"Great stay. Would stay again. "
United States
Weston B.
The price is ￥8,588
￥69,750 total
includes taxes & fees
Jan 27 - Jan 28, 2026
Seabreeze #4: Charming Cottage Footsteps to the Beach
On the beach
The Bridge at Soundview · Beach+OceanView+Sunrise

Apartment in Old Lyme

The Bridge at Soundview · Beach+OceanView+Sunrise
2.0 star property
10.0 out of 10, Exceptional, (1)
"The space was much larger than expected and was perfect for a group of 4 adults and 3 kids under 3! We had a great time, being a 5 minute walk from the beach and having a comfortable space to come back to. We'll definitely be coming back."
United States
Emotional J.
The price is ￥19,977
￥76,350 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Bridge at Soundview · Beach+OceanView+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.
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 Shelter Island Heights Hotel Reviews

Offshore Montauk

Offshore Montauk

10/10 Excellent
"robert the concierge is communicative , friendly and altogether charming "
Debra 2-night trip
Posted 9 hours ago
Offshore Montauk

Find out more about Shelter Island Heights

Search for holiday rentals in Shelter Island Heights on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island Heights using one of the methods below:

  • View our selection of featured holiday rentals in Shelter Island Heights
  • Use the map to find apartments and other holiday homes in the Shelter Island Heights neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island Heights while they last

Look no further and take a look at our great range of rental properties in Shelter Island Heights!

Frequently asked questions

Are there vacation rentals in Shelter Island Heights?

Yes, you can find vacation rentals close to the most popular attractions in Shelter Island Heights, or you can select a more remote option if you'd like a relaxing place to 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.

What's the top vacation rental that Shelter Island Heights has to offer?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : Visitors like this Shelter Island Heights vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Shelter Island Heights?

With 34 Expedia vacation rentals, you're sure 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 vacation rental in Shelter Island Heights like?

Vacation rentals are privately owned properties where you can stay for a long or short time in Shelter Island Heights. Vacation rentals feature amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.