Title: Shelter Island Vacation Rentals from $166: Search Short-Term Rentals | Expedia.com

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

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## Check prices for these dates

In two weeks

[Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 24 - Jul 26](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Shelter Island vacation rentals

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/2e009ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/8e3d5f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1-bedroom cottage with Grove Beach 🏖️ access.

[](https://www.expedia.com/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

Clinton

9.6/10

Exceptional

(40 reviews)

"Many local restaurants near by. Christy's for breakfast was very good. "

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

Benjamin H.

$159 nightly

$180 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Clinton-Hotels-1-Bedroom-Cottage-With-Grove-Beach-Access.h90991445.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/0bbae525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/185a0230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/035b4021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/c5a2aa07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

[](https://www.expedia.com/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information)

Waterford

10/10

Exceptional

(18 reviews)

"Wonderful place with a great location! Fantastic communication!"

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

Cary H.

$266 nightly

$301 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Waterford-Hotels-Cozy-Renovated-Cottage-With-Game-Room.h108765994.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/3f0d43b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/17c0663e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/4e5920d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/878d2c1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Bay Cottage · Rocky Neck Park, Beach & Niantic

[](https://www.expedia.com/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

East Lyme

9.0/10

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

Sarah G.

$391 nightly

$441 total

Apr 2 - Apr 3

Total with taxes and fees

[](https://www.expedia.com/Niantic-Hotels-The-Bay-Cottage-Rocky-Neck-Park.h109114296.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/116c6f59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/08e84186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/2c178ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/2c60a89e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Anchor at Soundview · Beach+Ocean+Sunrise

[](https://www.expedia.com/Old-Lyme-Hotels-The-Anchor-At-Soundview-BeachOceanViewSunrise.h106147917.Hotel-Information)

Old Lyme

8.0/10

Very Good

(2 reviews)

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

October P.

$173 nightly

$195 total

Apr 5 - Apr 6

Total with taxes and fees

[](https://www.expedia.com/Old-Lyme-Hotels-The-Anchor-At-Soundview-BeachOceanViewSunrise.h106147917.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/947697cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/9ddc24ce.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/106000000/105310000/105302000/105301933/0298db95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/bec199ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

Old Lyme

10/10

Exceptional

(6 reviews)

"Host was very responsive. Property as described. We would stay again! "

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

john18250

$394 nightly

$445 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/f0c0c2c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/e632266d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/724b2312.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium Tent, 1 Queen Bed | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/fe9ed1d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### North Fork Cottages & RV Resort

[](https://www.expedia.com/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information)

Greenport

8.6/10

Excellent

(11 reviews)

"great place to stay, clean and quiet....loved it"

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

Darlin

$181 nightly

$206 total

Apr 26 - Apr 27

Total with taxes and fees

[](https://www.expedia.com/Greenport-Hotels-North-Fork-Cottages-RV-Resort.h121214797.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/3f2f736d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/51264f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/b42f892a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/ab165773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Seabreeze 3 Cozy cottage by the beach

[](https://www.expedia.com/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information)

Hampton Bays

10/10

Exceptional

(1 review)

$445 nightly

$475 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hampton-Bays-Hotels-Water-Views-Cottage-Footsteps-To-Meschutt-Beach.h114533130.Hotel-Information)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/33a85d3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/8066b18d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/fda79bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/b32ce68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

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

Waterford

10/10

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

Brenda W.

$384 nightly

$433 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c88122e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/1e415396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/ef7e518d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/9825549c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### BlackBerry Private home with jacuzzi yearlong

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

East Hampton

9.0/10

Wonderful

(4 reviews)

"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.

$747 nightly

$800 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/3dd02542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/9b931aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oceanfront 2BD Queen and 2 Twins | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/2b9ce1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/213ea8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windward Shores Ocean Resort

[](https://www.expedia.com/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

Napeague

8.8/10

Excellent

(310 reviews)

"Amazing stay! Place was perfect and staff was so friendly."

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

Heather

$172 nightly

$197 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Amagansett-Hotels-Windward-Shores-Ocean-Resort.h4207136.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/ec2516ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Manor

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

Montauk

9.2/10

Wonderful

(1,309 reviews)

"Great property "

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

brian

$168 nightly

$192 total

Apr 14 - Apr 15

Total with taxes and fees

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

![Beach nearby](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/c3f938dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/72873cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/ffda393d.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)

### Insta-worthy Couples Retreat: Perfect for romantic getaway!

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

Old Lyme

9.4/10

Exceptional

(53 reviews)

"Adorable cottage. Nice location. "

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

Janet B.

$183 nightly

$207 total

Apr 7 - Apr 8

Total with taxes and fees

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

![Outdoor dining](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/a433371c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/a3f762f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/9aa58e22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, offices](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/1e9eca1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa Luz Cozy Family Home with Jacuzzi year round

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

Hampon Bays

9.6/10

Exceptional

(23 reviews)

"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.

$802 nightly

$854 total

Apr 2 - Apr 3

Total with taxes and fees

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

![Exterior detail](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/e12e0a29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/728215df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/a85d3539.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/ce1cf8e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shoreline Oasis

[](https://www.expedia.com/Shoreline-Oasis.h113308197.Hotel-Information)

Clinton

9.2/10

Wonderful

(7 reviews)

"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "

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

Tom S.

[](https://www.expedia.com/Shoreline-Oasis.h113308197.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/85d04a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/bebec502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/c66a667e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/e3540489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Floating Nest on Private River. Serene Views & Ultimate Relaxation

[](https://www.expedia.com/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information)

Old Lyme

$332 nightly

$376 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Old-Lyme-Hotels-Floating-Nest-On-Private-River-Serene-Views-Ultimate-Relaxation.h103095183.Hotel-Information)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/6d467d71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/a7c4d35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/d00906f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/167fb5a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hamptons apartment getaway

[](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.Hotel-Information)

East Quogue

6.0/10

(3 reviews)

"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "

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

Hilary K.

$251 nightly

$287 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.Hotel-Information)

![Beach nearby](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/8aaee58c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/fc0e0719.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/bb209788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436580/cd5e199d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

[](https://www.expedia.com/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information)

Westbrook Center

$228 nightly

$259 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Westbrook-Hotels-Private-2nd-Floor-Apt-4-Mins-To-Beach-EV-Charger-Parking-Included.h126436580.Hotel-Information)

![Condo | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/f965a09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/fa408cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Condo | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/a48d2d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/0090e01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cliffside Resort Condominiums

[](https://www.expedia.com/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.Hotel-Information)

Greenport

9.0/10

Wonderful

(249 reviews)

"Great stay - beautiful place"

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

Rebecca

$182 nightly

$208 total

Apr 29 - Apr 30

Total with taxes and fees

[](https://www.expedia.com/Greenport-Hotels-Cliffside-Resort-Condominiums.h10449005.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)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/021898ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/55b895af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beachside Bliss w/ Game Room, Gym & Golf Green

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

Westbrook

10/10

Exceptional

(1 review)

"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.

$458 nightly

$519 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/e52f4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/433807ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/6b6b7167.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

[](https://www.expedia.com/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.Hotel-Information)

Old Saybrook Center

9.6/10

Exceptional

(43 reviews)

"Lovely cottage! Enjoyed our stay! "

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

Joyce S.

[](https://www.expedia.com/Old-Saybrook-Hotels-Luxury-Cottage-Walking-Distance-To-Saybrook-Point-Marina.h72604611.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.com/Hotel-Search?startDate=2026-04-14&endDate=2026-04-15&regionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APART_HOTEL)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VACATION_HOME)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VILLA)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CONDO)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APARTMENT)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Shelter+Island%2C+New+York%2C+United+States+of+America&regionId=157359&latLong=41.068153%2C-72.338692&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

![Pier Blue Inn Old Saybrook - Essex](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/5cb2e3e0_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

2/10 Terrible

"My room was no where near clean. Not only was there multiple urine stains on the toilet seat, there was also a fecal stain that was also not cleaned IN the toilet. How do you not clean the TOILET? "

[](https://expedia.com/Old-Saybrook-Hotels-Pier-Blue-Inn-Old-Saybrook-Essex.h12143.Hotel-Information)

![Offshore Montauk](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6944012d_y.jpg)

### Offshore Montauk

10/10 Excellent

"Very clean room, good quality. The outside pool under construction as of March 2026\. "

[](https://expedia.com/Montauk-Hotels-The-Offshore.h113578409.Hotel-Information)

![Sound View Greenport](https://images.trvl-media.com/lodging/16000000/15280000/15273200/15273178/7aeccb7c_y.jpg)

### Sound View Greenport

8/10 Good

"it was ok"

[](https://expedia.com/Greenport-Hotels-Sound-View-Greenport.h15273178.Hotel-Information)

![Aqua by American Beech - Adults Only](https://images.trvl-media.com/lodging/25000000/24090000/24082000/24081913/70f0f9b2_y.jpg)

### Aqua by American Beech - Adults Only

10/10 Excellent

"This is my second time staying I love this place. It's a small place so it is very quiet and romantic setting on a private beach"

[](https://expedia.com/Riverhead-Hotels-Aqua-By-American-Beech.h24081913.Hotel-Information)

![Sag Harbor Inn](https://images.trvl-media.com/lodging/27000000/26500000/26497900/26497858/1c345cd0_y.jpg)

### Sag Harbor Inn

10/10 Excellent

"Clean room, nice breakfast options."

[](https://expedia.com/Sag-Harbor-Hotels-Sag-Harbor-Inn.h26497858.Hotel-Information)

![The Bentley Hotel Southampton](https://images.trvl-media.com/lodging/54000000/53970000/53963000/53962986/cc53a2c2_y.jpg)

### The Bentley Hotel Southampton

10/10 Excellent

"Loved the place, clean and helpfull staff."

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

![The Shoals Suites and Slips](https://images.trvl-media.com/lodging/77000000/76720000/76716300/76716269/5a27472c_y.jpg)

### The Shoals Suites and Slips

10/10 Excellent

"Simply delightful!"

[](https://expedia.com/Southold-Hotels-The-Shoals-Suites-And-Slips.h76716269.Hotel-Information)

![The Sagaponack](https://images.trvl-media.com/lodging/82000000/81150000/81143200/81143153/ce84672e_y.jpg)

### The Sagaponack

10/10 Excellent

"Wonderful! What a beautiful property, room and the location is perfection!"

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

![Water's Edge Resort & Spa](https://images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/fc6ee41c_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"Enjoyable stay. "

[](https://expedia.com/Old-Saybrook-Hotels-Waters-Edge-Resort-Spa.h9679841.Hotel-Information)

## Find out more about Shelter Island

**Everything you need to know about Shelter Island vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Shelter Island vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Shelter Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $166 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Shelter Island rentals**

At Expedia, we put the best Shelter Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
- All accommodation types in Shelter Island

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- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Shelter Island ](https://expedia.com/Shelter-Island-Private-Vacation-Homes.d157359-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Shelter Island ](https://expedia.com/Shelter-Island-Cottages.d157359-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Shelter Island ](https://expedia.com/Shelter-Island-Apartments.d157359-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Shelter Island ](https://expedia.com/Shelter-Island-Condos.d157359-aaCondos.Travel-Guide-Accommodation)
- [Villas in Shelter Island ](https://expedia.com/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation)
- [B&B in Shelter Island ](https://expedia.com/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Motels in Shelter Island ](https://expedia.com/Shelter-Island-Motels.d157359-aaMotels.Travel-Guide-Accommodation)
- [Resorts in Shelter Island ](https://expedia.com/Shelter-Island-Resorts.d157359-aaResorts.Travel-Guide-Accommodation)
- [RV Parks in Shelter Island ](https://expedia.com/Shelter-Island-RV-Parks.d157359-aaRVParks.Travel-Guide-Accommodation)
- [Aparthotels in Shelter Island ](https://expedia.com/Shelter-Island-Apart-Hotels.d157359-aaApartHotels.Travel-Guide-Accommodation)
- [Farmstay in Shelter Island ](https://expedia.com/Shelter-Island-Agritourism.d157359-aaAgritourism.Travel-Guide-Accommodation)
- [Inns in Shelter Island ](https://expedia.com/Shelter-Island-Inns.d157359-aaInns.Travel-Guide-Accommodation)
- [Houseboats in Shelter Island ](https://expedia.com/Shelter-Island-Houseboats.d157359-aaHouseboats.Travel-Guide-Accommodation)
- [Guest Houses in Shelter Island ](https://expedia.com/Shelter-Island-Guest-Houses.d157359-aaGuestHouses.Travel-Guide-Accommodation)
- [Cabin Rentals in Shelter Island ](https://expedia.com/Shelter-Island-Cabins.d157359-aaCabins.Travel-Guide-Accommodation)
- [Chalets in Shelter Island ](https://expedia.com/Shelter-Island-Chalets.d157359-aaChalets.Travel-Guide-Accommodation)
- [Hostels in Shelter Island ](https://expedia.com/Shelter-Island-Hostels.d157359-aaHostels.Travel-Guide-Accommodation)
- [Lodges in Shelter Island ](https://expedia.com/Shelter-Island-Lodges.d157359-aaLodges.Travel-Guide-Accommodation)
- [Condo Resorts in Shelter Island ](https://expedia.com/Shelter-Island-Condominium-Resort.d157359-aaCondominiumResort.Travel-Guide-Accommodation)
- [Residences in Shelter Island ](https://expedia.com/Shelter-Island-Residences.d157359-aaResidences.Travel-Guide-Accommodation)

## Frequently asked questions

### Can I find vacation rentals in Shelter Island?

### What are some of the best vacation home rentals that Shelter Island has to offer?

### How many vacation rentals are there in Shelter Island?

### What can I see and do in Shelter Island?

### What are vacation rentals like in Shelter Island?

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- [Hotels in Lake George](https://expedia.com/Lake-George-Hotels.d6055969.Travel-Guide-Hotels)
- [Hotels in Rhinebeck](https://expedia.com/Rhinebeck-Hotels.d55927.Travel-Guide-Hotels)
- [Hotels in Poughkeepsie](https://expedia.com/Poughkeepsie-Hotels.d6056317.Travel-Guide-Hotels)
- [Hotels in Middletown](https://expedia.com/Middletown-Hotels.d8864.Travel-Guide-Hotels)
- [Hotels in Hudson](https://expedia.com/Hudson-Hotels.d55762.Travel-Guide-Hotels)
- [Hotels in Niagara Falls](https://expedia.com/Niagara-Falls-Hotels.d602721.Travel-Guide-Hotels)
- [Hotels in Cooperstown](https://expedia.com/Cooperstown-Hotels.d6487.Travel-Guide-Hotels)
- [Hotels in Utica](https://expedia.com/Utica-Hotels.d6055801.Travel-Guide-Hotels)
- [Hotels in Yonkers](https://expedia.com/Yonkers-Hotels.d7789.Travel-Guide-Hotels)

Flights

- [Flights to Albany](https://expedia.com/Cheap-Flights-To-Albany.d603260.Travel-Guide-Flights)
- [Flights to Niagara Falls](https://expedia.com/Cheap-Flights-To-Niagara-Falls.d602721.Travel-Guide-Flights)
- [Syracuse Flights](https://expedia.com/lp/flights/601764/flights-from-syracuse)
- [Flights to Syracuse](https://expedia.com/Cheap-Flights-To-Syracuse.d601764.Travel-Guide-Flights)

Cars

- [Car rentals in Albany](https://expedia.com/Car-Rentals-In-Albany.d603260.Car-Rental-Guide)
- [Car rentals in Syracuse](https://expedia.com/Car-Rentals-In-Syracuse.d601764.Car-Rental-Guide)

Activities

- [Things to do in Niagara Falls](https://expedia.com/Things-To-Do-In-Niagara-Falls.d602721.Travel-Guide-Activities)

Packages

- [Niagara Falls Vacation](https://expedia.com/Niagara-Falls.d602721.Destination-Travel-Guides)

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