Shelter Island Heights Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Shelter Island Heights holiday rentals

Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is HK$1,544
HK$1,763 total
includes taxes & fees
8 Apr - 9 Apr
North Fork Cottages & RV Resort
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is HK$1,162
HK$1,541 total
includes taxes & fees
6 Apr - 7 Apr
Windward Shores Ocean Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is HK$1,129
HK$1,630 total
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,310 reviews)
"Great property "
United States
brian
The price is HK$1,185
HK$1,508 total
includes taxes & fees
5 May - 6 May
Montauk Manor
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$626
HK$1,550 total
includes taxes & fees
6 Apr - 7 Apr
The Stern at Soundview · Beach+Ocean+Sunrise
Living area

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is HK$4,303
HK$5,812 total
includes taxes & fees
6 Apr - 7 Apr
Offshore Residences
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 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 HK$1,313
HK$3,368 total
includes taxes & fees
8 Apr - 9 Apr
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Living area

Newly Renovated Sag Harbor Beach House with Pool

Newly Renovated Sag Harbor Beach House with Pool
Sag Harbor
The price is HK$2,547
HK$5,776 total
includes taxes & fees
9 Apr - 10 Apr
Newly Renovated Sag Harbor Beach House with Pool
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, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is HK$939
HK$3,488 total
includes taxes & fees
6 Apr - 7 Apr
Rogers Lake House (87) · CT College+Beach+USCGA
Interior

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is HK$1,764
HK$2,943 total
includes taxes & fees
6 Apr - 7 Apr
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Terrace/patio

Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
The price is HK$1,543
HK$3,236 total
includes taxes & fees
6 Apr - 7 Apr
Direct Lakefront - Stunning Views and Panoramic Sunsets
Living area

PinkWood PlayHouse

PinkWood PlayHouse
4.0 star property
East Hampton
The price is HK$23,516
HK$26,867 total
includes taxes & fees
7 Apr - 8 Apr
PinkWood PlayHouse
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, (19 reviews)
"Wonderful place with a great location! Fantastic communication!"
United States
Cary H.
The price is HK$1,072
HK$2,378 total
includes taxes & fees
7 Apr - 8 Apr
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Outdoor dining

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (126 reviews)
"Great property!"
United States
Matthew B.
The price is HK$2,312
HK$4,513 total
includes taxes & fees
12 Apr - 13 Apr
Coastal New England Waterfront Home, Harkness Park, Casinos
Property grounds

Beachfront Greenport Villa

Beachfront Greenport Villa
Greenport
9.8 out of 10, Exceptional, (11 reviews)
"Super location - just near The beautiful village of Greenport with a sweeping view of the bay, A very happy house - super Clean, and we had everything that we needed. Meghan was a wonderful host, and answered us quickly with any question that we had. I loved the NorthFork and this home was the perfect place to stay!"
United States
Carine J.
Beachfront Greenport Villa
1 bedroom, free WiFi, bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$957
HK$1,996 total
includes taxes & fees
7 Apr - 8 Apr
Lakefront Boho Tiny House
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is HK$1,164
HK$2,250 total
includes taxes & fees
28 Apr - 29 Apr
Cozy Lakefront Tiny House
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, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is HK$1,263
HK$3,506 total
includes taxes & fees
7 Apr - 8 Apr
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Interior

Cozy Hamptons Escape 3BR Minutes From Beach!

Cozy Hamptons Escape 3BR Minutes From Beach!
Hampton Bays
9.2 out of 10, Wonderful, (5 reviews)
"Great place. It's exactly like the listing! Would stay again!"
United States
Taylor H.
The price is HK$9,406
HK$12,278 total
includes taxes & fees
6 Apr - 7 Apr
Cozy Hamptons Escape 3BR Minutes From Beach!
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$1,121
HK$3,972 total
includes taxes & fees
7 Apr - 8 Apr
Beachside Bliss w/ Game Room, Gym & Golf Green
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

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

6/10 Okay
"Room was clean…ish. Food was alright but overpriced for what it was. Amenities were the highlight. Overall good experience but could have been had at much lower of a price tag."
Mohanram 2-night trip
Posted 14 hours ago
Gurney's Montauk Resort & Seawater Spa

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.

What are some of the best holiday rentals that Shelter Island Heights has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Shelter Island Heights is located on the beach, and has an outdoor pool, a fireplace and a BBQ 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 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.