Title: Shelter Island Vacation Home Rentals from CA $355: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[Shelter Island Travel Guide](https://expedia.ca/Shelter-Island.dx157359)[Hotels in Shelter Island](https://expedia.ca/Shelter-Island-Hotels.d157359.Travel-Guide-Hotels)[Vacation Rentals in Shelter Island](https://expedia.ca/Shelter-Island-Vacation-Rentals.d157359.Travel-Guide-VacationRentals)[Flights to Shelter Island](https://expedia.ca/Cheap-Flights-To-Shelter-Island.d157359.Travel-Guide-Flights)[Things to do in Shelter Island](https://expedia.ca/Things-To-Do-In-Shelter-Island.d157359.Travel-Guide-Activities)[Shelter Island Car Rentals](https://expedia.ca/Car-Rentals-In-Shelter-Island.d157359.Car-Rental-Guide)[Shelter Island Vacation Packages](https://expedia.ca/Shelter-Island.d157359.Destination-Travel-Guides)

![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Shelter Island Vacation Rentals

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## Check prices for these dates

In two weeks

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Shelter Island Vacation Homes

![Property grounds](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/7033cd48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, in-room safe, desk, free WiFi](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/24362044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/f2189685.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/a1d1bd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Shelter Island

10/10

Exceptional

(52)

"Really great property, had a relaxing lovely time!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nava S.

CA $1,015

CA $1,876 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Shelter-Island-Hotels-Work-And-Play-Special-Extended-Stay-Discount-At-A-Hideaway-With-Stellar-Wifi.h39934446.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/f7b0c3cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/0c0a866f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/4ed75f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/669e9fe2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Lyme

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Nicole B.

CA $121

CA $566 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Old-Lyme-Hotels-Rogers-Lake-House.h105301933.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/1c55c50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/5860a5b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/544c1919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/d4679987.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

10/10

Exceptional

(10)

"We had a nice stay. Kitchen well stocked and house was clean and comfortable."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Elaine A.

CA $132

CA $506 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/f20bc122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8791fbfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8ea39820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/00b024ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampton Bays

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Coleman H.

CA $140

CA $1,700 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Hampton-Bays-Hotels-Unique-Location-Fenced-In-Private-Beach.h92502496.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/53aab435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/fbefb98b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/f9f66e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/6fccc75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Lyme

9.6/10

Exceptional

(52)

"Great stay, charming cottage, hope to return"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ellen C.

CA $137

CA $355 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Old-Lyme-Hotels-Insta-Worthy-Couples-Retreat-Perfect-For-Romantic-Getaway.h52069712.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/891accf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/a0e54ecb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/623abb73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westbrook

10/10

Exceptional

(1)

"Perfect house for 6 guests. Loved that it was close to the beach."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shannon G.

CA $201

CA $723 total

includes taxes & fees

Dec 9 - Dec 10

[](https://www.expedia.ca/Westbrook-Hotels-Beachside-Bliss-W-Game-Room.h121396426.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/4ecca3ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/809e0319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/864047ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/a53b6f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Hampton

9.0/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Suzanne R.

CA $78

CA $1,206 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/East-Hampton-Hotels-Fall-In-Love-In-East-Hampton.h71000754.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/47172b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/6ca48340.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/02ffbf91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/3f78326f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampon Bays

9.6/10

Exceptional

(22)

"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Annie B.

CA $140

CA $1,792 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Hampton-Bays-Hotels-Private-Completely-Fenced-In-Property-Near-Beach.h66472313.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/8c60ece7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/2a31845e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/f4c65ca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/00ea4ccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

10/10

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](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kelly Z.

CA $202

CA $429 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Clinton-Hotels-Stylish-Modern-Stay-Steps-From-The-Ocean.h120150878.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/b3f1fe2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/3368cbed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/441cf856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/79000000/78750000/78740400/78740383/cee0fa4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Water Mill

10/10

Exceptional

(6)

"Highly recommend everything from start to finish went smoothly and it was a great experience!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie M.

CA $5,707

CA $10,193 total

includes taxes & fees

Nov 22 - Nov 23

[](https://www.expedia.ca/Water-Mill-Hotels-Ultimate-Water-Mill-Southampton-Escape-Stunning-7BR-Estate-For-Family-Friends.h78740383.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/1c33ad63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/ca0fd6c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/9b6d9dce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99410000/99406900/99406822/f3beb059.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Westbrook Center

9.4/10

Exceptional

(14)

"Very nice small place to stay by the beach and close to great coffee shop. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Donovan V.

CA $245

CA $587 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Westbrook-Hotels-Adorable-Cottage.h99406822.Hotel-Information)

![Beach](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/f6c15885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/126bef9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/d416d8d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/114000000/113540000/113530200/113530184/b7d556ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sag Harbor

CA $5,618

CA $9,058 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Sag-Harbor-Hotels-Spacious-5-Bedroom-House-With-Water-Views-And-2-Houses-From-The-Bay.h113530184.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/f8cef332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h954x0y0-9b5015ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h953x0y0-69414cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/19000000/18770000/18762100/18762073/w1283h960x0y0-cce9554c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Saybrook Manor

9.6/10

Exceptional

(133)

"Like a trip to 1800 but with AC. Amazing place. Didn’t want to leave, but will come back. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rob C.

CA $281

CA $723 total

includes taxes & fees

Dec 22 - Dec 23

[](https://www.expedia.ca/Old-Saybrook-Hotels-Capt-Nathaniel-Clarke-Historic-Homestead.h18762073.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/99132894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/f0c859fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/d639410c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/24000000/23150000/23145000/23144923/4c3022eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Waterford

10/10

Exceptional

(126)

"Repeat renter! Great location, super clean house, A host: very responsive; will be back again! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carrie B.

CA $464

CA $874 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Waterford-Hotels-Coastal-New-England-Waterfront-Home.h23144923.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0195b6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/e500d985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/9e0f05a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

9.0/10

Wonderful

(4)

"Great job "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

emilio

CA $251

CA $390 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.Hotel-Information)

![5 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/7a209baf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/8f1986e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/b061fa88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/114000000/113440000/113439500/113439409/f8c8a8d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bay Point

CA $6,320

CA $8,976 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Sag-Harbor-Hotels-Sag-Harbor-Water-View-W-Dock.h113439409.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/123000000/122860000/122852700/122852694/ed866d96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/123000000/122860000/122852700/122852694/def5d864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/123000000/122860000/122852700/122852694/7a879baa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122860000/122852700/122852694/737180e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Clinton

CA $225

CA $288 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Clinton-Hotels-House-In-Clinton.h122852694.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/b8434d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/e51e1447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/4bc52833.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/86000000/85380000/85374000/85373907/305503f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hampton Bays

10/10

Exceptional

(5)

"Clean and fully updated home situated on a canal with a partial view of the bay . A perfect location ."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michael L.

CA $456

CA $902 total

includes taxes & fees

Nov 25 - Nov 26

[](https://www.expedia.ca/Hampton-Bays-Hotels-Immaculate-Waterfront-2-Bedroom.h85373907.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/10ef3e76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/5f36ce70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/52e5aba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113100000/113098300/113098265/a12114d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southold

10/10

Exceptional

(3)

"good experience"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Anonymous traveller

CA $843

CA $1,650 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Southold-Hotels-Magic-Place.h113098265.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/c3191410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/e7a48081.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/47cbdcfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/105000000/104830000/104820900/104820817/0defc87a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Southampton

10/10

Exceptional

(3)

"perfect for families"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Okito H.

CA $634

CA $1,563 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Southampton-Hotels-Renovated-Hamptons-4-Bedroom.h104820817.Hotel-Information)

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](https://expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&regionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Private vacation homes

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Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=APARTMENT)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=CONDO)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=COTTAGE)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-02-19&d1=2026-02-19&endDate=2026-02-22&d2=2026-02-22&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

![Montauk Blue Hotel](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e_y.jpg)

### Montauk Blue Hotel

10/10 Excellent

"I always have a 5/5 stay at Montauk Blue. "

[](https://expedia.ca/Montauk-Hotels-Montauk-Blue-Hotel.h105612509.Hotel-Information)

![Bayview Resort](https://images.trvl-media.com/lodging/11000000/10460000/10453900/10453825/5ed206f2_y.jpg)

### Bayview Resort

10/10 Excellent

"Just right. "

[](https://expedia.ca/Hampton-Bays-Hotels-Bayview-Resort.h10453825.Hotel-Information)

![Quality Inn Old Saybrook - Westbrook](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/228c4607_y.jpg)

### Quality Inn Old Saybrook - Westbrook

10/10 Excellent

"Staff was kind. Easy, comfortable stay."

[](https://expedia.ca/Old-Saybrook-Hotels-Quality-Inn-Old-Saybrook-Westbrook.h3988.Hotel-Information)

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/5e605108_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Everything and everyone was fabulous! "

[](https://expedia.ca/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.Hotel-Information)

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/46cd22ca_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Location! Location! Location! Watched the sunrise from my bed this am. Amazing "

[](https://expedia.ca/Greenport-Hotels-The-Harborfront-Inn.h43532300.Hotel-Information)

![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/d64f35e8_y.jpg)

### The Sagaponack

10/10 Excellent

"Beautiful room, loved the treats at the galley."

[](https://expedia.ca/Wainscott-Hotels-The-Wainscott-Inn.h81143153.Hotel-Information)

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/895004c9_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"They gave us a room upgrade which was unexpected, the room has a great view of the ocean which made our stay extra special. "

[](https://expedia.ca/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/60534d98_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Nice"

[](https://expedia.ca/Southampton-Hotels-Bentley-Southampton.h53962986.Hotel-Information)

![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a_y.jpg)

### Montauk Manor

10/10 Excellent

"Our room was decorated nicely and larger than we expected. "

[](https://expedia.ca/Montauk-Hotels-Montauk-Manor.h12694044.Hotel-Information)

## Find out more about Shelter Island

## Shelter Island Vacation Homes information

| Number of reviews | 365 |
| --- | --- |
| Accommodation | 1860 Vacation Homes |
| Lowest Price | CA $355 |
| Highest Price | CA $10,193 |

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-   [Silver Beach Hotels](https://www.expedia.ca/Silver-Beach-Shelter-Island-Hotels.0-n553248635976481903-0.Travel-Guide-Filter-Hotels)
-   [Cheap Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Cheap-Hotels.0-0-d183719-tCheapHotels.Travel-Guide-Filter-Hotels)
-   [Romantic Hotels in Southold](https://www.expedia.ca/Southold-Hotels-Romantic-Hotel.0-0-d183719-tRomanticHotel.Travel-Guide-Filter-Hotels)
-   [Southold Hotels](https://www.expedia.ca/Southold-Hotels.d183719.Travel-Guide-Hotels)
-   [Motels in Southold](https://www.expedia.ca/Southold-Motels.d183719-aaMotels.Travel-Guide-Accommodation)
-   [Hotels near Sunset Beach](https://www.expedia.ca/Sunset-Beach-Hotels.0-l553248626388141313-0.Travel-Guide-Filter-Hotels)
-   [The Heights Hotels](https://www.expedia.ca/The-Heights-Shelter-Island-Heights-Hotels.0-n553248635976473534-0.Travel-Guide-Filter-Hotels)
-   [Hotels near Wades Beach](https://www.expedia.ca/Wades-Beach-Hotels.0-l553248621554204759-0.Travel-Guide-Filter-Hotels)

-   [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
-   [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
-   [Flights from North Haven](https://www.expedia.ca/lp/flights/553248634998589872/flights-from-north-haven)
-   [Flights from East Marion](https://www.expedia.ca/lp/flights/6069914/flights-from-east-marion)
-   [Flights from Orient](https://www.expedia.ca/lp/flights/6326191/flights-from-orient)
-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

-   [Visit East Marion](https://www.expedia.ca/East-Marion.dx6069914)
-   [Visit Pipes Cove](https://www.expedia.ca/Greenport-Pipes-Cove.dx553248635976473295)
-   [Kontokosta Winery](https://www.expedia.ca/Kontokosta-Winery-Greenport.d6326928.Vacation-Attraction)
-   [Visit North Haven](https://www.expedia.ca/North-Haven.dx553248634998589872)
-   [Orient Vacations](https://www.expedia.ca/Orient.d6326191.Destination-Travel-Guides)
-   [Visit Bay Point](https://www.expedia.ca/Sag-Harbor-Bay-Point.dx553248635976471151)
-   [Visit Sag Harbor](https://www.expedia.ca/Sag-Harbor.dx154327)
-   [Shelter Island Heights Vacations](https://www.expedia.ca/Shelter-Island-Heights.d183716.Destination-Travel-Guides)

-   [Car rental Greenport](https://www.expedia.ca/Car-Rentals-In-Greenport.d110728.Car-Rental-Guide)
-   [Car rental Orient](https://www.expedia.ca/Car-Rentals-In-Orient.d6326191.Car-Rental-Guide)

-   [Things to do in Greenport](https://www.expedia.ca/Things-To-Do-In-Greenport.d110728.Travel-Guide-Activities)
-   [Things to do in Sag Harbor](https://www.expedia.ca/Things-To-Do-In-Sag-Harbor.d154327.Travel-Guide-Activities)
-   [Things to do in Shelter Island Heights](https://www.expedia.ca/Things-To-Do-In-Shelter-Island-Heights.d183716.Travel-Guide-Activities)

-   [Book Vacation Homes in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation)