Photo by Brian V. Rowe

Shelter Island Heights Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 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, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is HK$1,079
HK$1,385 total
includes taxes & fees
8 Dec - 9 Dec
Montauk Manor
Beach nearby
Cliffside Resort Condominiums

Aparthotel in Greenport

3.0 star property
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Private kitchen
Montauk Oceanside Suites

Aparthotel in Downtown Montauk

3.0 star property
8.6 out of 10, Excellent, (418)
"Great spot- walkable and nice accommodations! "
United States
Lesley
Montauk Oceanside Suites
TV, fireplace, video library, stereo
Stunning Hampton Holiday Family Fantasy for your Team

Holiday Home in East Hampton

9.8 out of 10, Exceptional, (74)
"Outstanding house, beautifully maintained and well stocked, with great location."
United States
Jason C.
Stunning Hampton Holiday Family Fantasy for your Team
Outdoor pool, a heated pool
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Holiday Home in Sag Harbor

10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available
Exterior
Shoreline Oasis

Apartment in Clinton

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 HK$1,393
HK$2,028 total
includes taxes & fees
15 Dec - 16 Dec
Shoreline Oasis
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, (14)
"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 HK$1,109
HK$2,435 total
includes taxes & fees
8 Dec - 9 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Outdoor pool, a heated pool
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Holiday Home in Southampton

9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Exterior
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Apartment in Madison

10.0 out of 10, Exceptional, (36)
"We had a wonderful time here!! "
United States
Leslie S.
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn
Pool
Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views

Villa in New London

10.0 out of 10, Exceptional, (45)
"Comfortable and very spacious house - was great for our family reunion. Close to lots of fun things and nice views of water. "
United States
zachary b.
The price is HK$3,619
HK$7,194 total
includes taxes & fees
8 Dec - 9 Dec
Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views
Smart TV, fireplace, stereo
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

Holiday Home in East Hampton

10.0 out of 10, Exceptional, (95)
"Great stay and great communication! "
United States
Nicole S.
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings
Fridge, microwave, oven, stovetop
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

Holiday Home in East Hampton

9.6 out of 10, Exceptional, (39)
"Beautiful house! Great area! Great host!"
United States
brooke v.
STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH
Private kitchen
Driftwood Resort

Condo in Montauk

3.5 star property
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort
Living area
Offshore Residences

Condo in Downtown Montauk

4.5 star property
The price is HK$3,728
HK$5,149 total
includes taxes & fees
7 Dec - 8 Dec
Offshore Residences
On the beach
The Bridge at Soundview · Beach+OceanView+Sunrise

Apartment in Old Lyme

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 HK$993
HK$3,796 total
includes taxes & fees
6 Dec - 7 Dec
The Bridge at Soundview · Beach+OceanView+Sunrise
Fridge, microwave, oven, dishwasher
Large Charming Historic House close to Beaches

Holiday Home in Clinton

9.8 out of 10, Exceptional, (35)
"The house was very comfortable and we loved the historic qualities of the house and the convenient location. It was perfect for our family to all stay together while attending my niece's wedding."
United States
Sandra L.
Large Charming Historic House close to Beaches
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 HK$476
HK$1,303 total
includes taxes & fees
9 Dec - 10 Dec
1-bedroom cottage with Grove Beach 🏖️ access.
On the beach, sun-loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Holiday Home in Montauk

9.8 out of 10, Exceptional, (108)
"Home suited us perfectly for a 10-day vacation with family and friends. The back yard is absolutely fantastic and was perfect for summer grill-outs and pool days. The neighborhood is very quiet and location was spot-on just a 5 minute walk to the beach. Can’t say enough good things about Carter’s home - even better than the pictures!! "
United States
Katie M.
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Outdoor pool, a heated pool
A Quiet Place in the Hamptons

Holiday Home in East Quogue

9.6 out of 10, Exceptional, (39)
"Fantastic house for the extended family ! We loved the pool , enjoyed bbq grilling and hanging out together! "
United States
Anonymous traveller
A Quiet Place in the Hamptons
1 bedroom, WiFi, bed sheets
Unobstructed Ocean Views ! A Beautiful Montauk Getaway

Holiday Home in Montauk

10.0 out of 10, Exceptional, (62)
"Amazing stay…. Great host, excellent location and very clean!"
Australia
Amy W.
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
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

The Sagaponack

The Sagaponack

10/10 Excellent
"Clean & amenities, staff friendly Thank you "
Archil 1-night trip
Posted 2 days ago
The Sagaponack

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 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 34 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.