A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Shelter Island Heights vacation rentals

1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥24,677
￥43,930 total
includes taxes & fees
Jul 23 - Jul 24
1-bedroom cottage with Grove Beach 🏖️ access.
1 bedroom, bed sheets

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

Safari Tent Glamping,S10-CedarPt, East Hampton, NY
East Hampton
The price is ￥34,869
￥52,816 total
includes taxes & fees
Jul 22 - Jul 23
Safari Tent Glamping,S10-CedarPt, East Hampton, NY
Sun loungers, beach towels

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
The price is ￥25,553
￥58,549 total
includes taxes & fees
Jul 20 - Jul 21
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Smart TV, books

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

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
The price is ￥26,590
￥81,587 total
includes taxes & fees
Jul 16 - Jul 17
Rogers Lake House (87) · CT College+Beach+USCGA
1 bedroom, bed sheets

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 ￥34,869
￥52,816 total
includes taxes & fees
Jul 22 - Jul 23
Safari Tent Glamping,S5-CedarPt, East Hampton, NY
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (30 reviews)
"Great stay & great staff!"
United States
James
The price is ￥60,398
￥69,005 total
includes taxes & fees
Jul 29 - Jul 30
North Fork Resort
1 bedroom, WiFi (free), bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is ￥30,874
￥55,664 total
includes taxes & fees
Aug 12 - Aug 13
Lakefront Boho Tiny House
1 bedroom, bed sheets

Safari Tent Glamping,S7-CedarPt, East Hampton, NY

Safari Tent Glamping,S7-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (1 review)
"Thank you Cedar Point for the great accommodations. We were fortunate to have a Tent right on the Bay, great views and good times."
United States
Vasilios
The price is ￥34,869
￥52,816 total
includes taxes & fees
Jul 22 - Jul 23
Safari Tent Glamping,S7-CedarPt, East Hampton, NY
Living area

The Beach Nest-Lux Cottage Steps to the Beach

The Beach Nest-Lux Cottage Steps to the Beach
Clinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
United States
Karol W.
The price is ￥40,154
￥94,931 total
includes taxes & fees
Jul 19 - Jul 20
The Beach Nest-Lux Cottage Steps to the Beach
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is ￥28,854
￥52,883 total
includes taxes & fees
Jul 19 - Jul 20
The Stern at Soundview · Beach+Ocean+Sunrise
Beach nearby

Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (2 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is ￥29,901
￥54,247 total
includes taxes & fees
Jul 16 - Jul 17
Keel at Soundview · Beach+OceanView+Sunrise
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is ￥33,908
￥59,639 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Lakefront Tiny House
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
8.8 out of 10, Excellent, (6 reviews)
"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 ￥38,474
￥84,263 total
includes taxes & fees
Jul 20 - Jul 21
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (59 reviews)
"My family and I had an ideal stay at Kristine's beachside cottage. Highlights include a short walk to the beach, a well stocked kitchen, easy and efficient temperature controls and my kids especially loved the bunk beds! It was perfectly cozy and comfy for a family of four. We stayed here in April, but I can only imagine how lovely the screened in porch and back deck would feel during warmer months. 5 stars!"
United States
Leila N.
The price is ￥35,044
￥66,072 total
includes taxes & fees
Aug 9 - Aug 10
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Interior

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

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (28 reviews)
"The stay was great and the host was more than kind and very helpful! "
United States
Jenna K.
The price is ￥50,522
￥86,330 total
includes taxes & fees
Jul 19 - Jul 20
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Outdoor dining

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6

Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
Southampton
9.6 out of 10, Exceptional, (7 reviews)
"great experience"
United States
Jordan
The price is ￥56,784
￥95,275 total
includes taxes & fees
Jul 20 - Jul 21
Light, Airy, Wood-floors, 1 mile from Southampton Village, Pet Friendly, sleep 6
1 bedroom, bed sheets

Safari Tent Glamping,S11-CedarPt, East Hampton, NY

Safari Tent Glamping,S11-CedarPt, East Hampton, NY
East Hampton
10.0 out of 10, Exceptional, (2 reviews)
"Our tent was spacious and the bed was very comfortable with an incredible view of the harbor. Dave and Lee were very gracious and helpful. We especially enjoyed the Camp Store and the delicious omelets. Plus - how quiet and peaceful it was!"
United States
Lee
The price is ￥34,869
￥52,816 total
includes taxes & fees
Jul 27 - Jul 28
Safari Tent Glamping,S11-CedarPt, East Hampton, NY
Outdoor dining

Villa Luz Family Home w/ heated pool & jacuzzi

Villa Luz Family Home w/ heated pool & jacuzzi
Hampon Bays
9.6 out of 10, Exceptional, (25 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is ￥69,276
￥336,824 total
includes taxes & fees
Jul 19 - Jul 20
Villa Luz Family Home w/ heated pool & jacuzzi
Smart TV, fireplace, books

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, (12 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is ￥45,012
￥96,842 total
includes taxes & fees
Aug 13 - Aug 14
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
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

Zey Hotel

Zey Hotel

10/10 Excellent
"Staying at the Zey Hotel was comfortable, convenient to town and restaurants, and a lovely relaxing setting at the hotel both inside and outside in the garden. My room was spacious, and I appreciated that the hotel was dog-friendly so my well-behaved pup could be with me. I will stay here again when in the area."
Karen 1-night trip
Posted 6 hours ago
Zey Hotel

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
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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?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : Visitors like this Shelter Island Heights vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Shelter Island Heights?

With 31 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.