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 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 17 - Jul 19](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-07-17&endDate=2026-07-19&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)

![Property grounds](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/a654b98c.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)

![Exterior detail](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/b4ee006e.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

(38 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.

$177 nightly

$201 total

Mar 26 - Mar 27

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)

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

![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108770000/108766000/108765994/f3aa91d0.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

(17 reviews)

"Convenient location. The property had everything we needed for a one-night stay. "

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

Jane E.

$267 nightly

$302 total

Mar 25 - Mar 26

Total with taxes and fees

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

![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)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/79000000/78360000/78355300/78355230/d4ad42a8.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)

### 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.

$365 nightly

$412 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/Waterford-Hotels-Shore-Drive-2-Bedroom2-BathBunkQueen-Oasis.h78355230.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](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147917/fcccb3b4.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.

$186 nightly

$210 total

Mar 29 - Mar 30

Total with taxes and fees

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

![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)

![Property map](https://images.trvl-media.com/lodging/122000000/121220000/121214800/121214797/b50e5baa.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)

### 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

$175 nightly

$200 total

Apr 8 - Apr 9

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)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/2d4d8efa.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)

![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)

### 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)

$435 nightly

$463 total

Mar 25 - Mar 26

Total with taxes and fees

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

![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)

![West Studio Queen and Full | Living area | TV](https://images.trvl-media.com/lodging/5000000/4210000/4207200/4207136/fcfe3def.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)

### 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

$167 nightly

$190 total

Mar 25 - Mar 26

Total with taxes and fees

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

![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)

![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/259b8f45.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)

### 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

(5 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

$410 nightly

$463 total

Mar 29 - Mar 30

Total with taxes and fees

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

![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)

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

### 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.

$250 nightly

$283 total

Apr 13 - Apr 14

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/c66a667e.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)

![Marina](https://images.trvl-media.com/lodging/104000000/103100000/103095200/103095183/eb388ab1.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

Mar 25 - Mar 26

Total with taxes and fees

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

![Aerial view](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/aa464430.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)

![Garden](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/8f0a0367.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

(1,307 reviews)

"Great property "

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

brian

$168 nightly

$192 total

Apr 7 - Apr 8

Total with taxes and fees

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

![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)

![4 bedrooms, travel crib, free WiFi, bed sheets](https://images.trvl-media.com/lodging/72000000/71010000/71000800/71000754/c4935334.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.

$623 nightly

$663 total

Mar 25 - Mar 26

Total with taxes and fees

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

![Property grounds](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/9e16b0d1.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)

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

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/6f35c24c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stylish Modern Stay Steps from the Ocean

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

Clinton

10/10

Exceptional

(1 review)

"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.

$230 nightly

$261 total

Mar 25 - Mar 26

Total with taxes and fees

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

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

![Smart TV](https://images.trvl-media.com/lodging/114000000/113310000/113308200/113308197/1f01f033.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)

### 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.

$229 nightly

$260 total

Apr 1 - Apr 2

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8e05d72c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor banquet area](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/7ea21252.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/166abcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/8bfba2cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Black Swan Beachfront Home with Jacuzzi year round

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

Hampton Bays

9.8/10

Exceptional

(16 reviews)

"Nice house. Photos and descriptions represent it very accurately. "

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

Will K.

$798 nightly

$849 total

Mar 25 - Mar 26

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/1bd85de8.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)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72610000/72604700/72604611/825be1b5.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.

$440 nightly

$498 total

Mar 25 - Mar 26

Total with taxes and fees

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

![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)

![Living area](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/1c400db4.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)

### 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.

$436 nightly

$493 total

Mar 25 - Mar 26

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/67000000/66480000/66472400/66472313/4235c401.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)

![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

Mar 29 - Mar 30

Total with taxes and fees

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

![TV, fireplace, stereo, offices](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/9626c6fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/3e9c1103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/830deaf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123140000/123130500/123130471/0a29c96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### East Hampton Estate for 8, Sauna, Soaking Tub, Chef\`s Kitchen, Outdoor Fireplace

[](https://www.expedia.com/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.Hotel-Information)

East Hampton North

$729 nightly

$777 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/East-Hampton-Hotels-Serene-East-Hampton-Escape.h123130471.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)

![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/8e03b24b.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.

$249 nightly

$284 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/East-Quogue-Hotels-Hamptons-Apartment-Getaway.h92415894.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=2026-04-07&endDate=2026-04-08&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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APART_HOTEL)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CONDO)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APARTMENT)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA)

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=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

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

### The Bentley Hotel Southampton

10/10 Excellent

"Very good "

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

8/10 Good

"The room was clean and good. However, the sound insulation is really bad, I could hear people talking in the other room all night. "

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

![Gurney's Montauk Resort & Seawater Spa](https://images.trvl-media.com/lodging/8000000/7040000/7033800/7033726/b29cbb53_y.jpg)

### Gurney's Montauk Resort & Seawater Spa

2/10 Terrible

"Unfortunately our experience here was far below expectations! Please keep in mind the self proclaimed “luxury resort” has nothing to offer. Their amenities such as the pool and hot tubs were out of order. This was not communicated until check in. Keep in mind it was raining so the beach in a cold March rain was not an option. When confronting the staff about not informing their guests in advance, they said they still had the steam room and sauna to use however at 7 months pregnant I am unable to use these amenities. They also put us on the top floor resulting in climbing many stairs, which normally would be fine but not in my current condition. They did not seem the care. They have surprise alarm clocks that go off at 6AM and then start very loud construction at 6:30 AM. As well it was raining the whole time we were there so we had the unfortunate discovery that their stair cases becomes very slippery and flood in the rain! Again I am7 months pregnant now navigating three flights of flooded, slippery stairs. The front desk was no helpful and I emailed the manager for a resolution however he waited until we checked out to email me back therefor offering no solutions to our current stay and the only thing he could offer was a discount for a future stay. Why would we want to come back. This hotel does not accommodate pregnant people!! STAY AWAY!"

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

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

### Sound View Greenport

8/10 Good

"Lovely hotel. Amazing location. Gorgeous views. Breakfast was good continental. It rained hard and we had some water leaking in the door from the back deck. Mentioned it to the front desk when we checked out. Could’ve posed a Could’ve posed a slipping hazard.Otherwise, I would’ve given five stars. "

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

"Clean, spacious and thoughtful room amenities. Close by to town and great restaurants. "

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

"Very pleasurable experience here. It’s not something we’ll do every year, as it is expensive. Spa services are especially expensive. Nonetheless, the staf performed flawlessly. Food was excellent. Grounds were well cared for."

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

![Montauk Manor](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/4be91ce8_y.jpg)

### Montauk Manor

10/10 Excellent

"Everything was lovely. It was a wonderful place to relax after a long day of sightseeing. "

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

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

### The Sagaponack

10/10 Excellent

"Great property"

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

![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

4/10 Poor

"Loud room was what it looked like in the pics. Cold "

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

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- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [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

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- [Hotels in Albany](https://expedia.com/Albany-Hotels.d603260.Travel-Guide-Hotels)
- [Hotels in Beacon](https://expedia.com/Beacon-Hotels.d6173904.Travel-Guide-Hotels)
- [Hotels in White Plains](https://expedia.com/White-Plains-Hotels.d603214.Travel-Guide-Hotels)
- [Hotels in Watkins Glen](https://expedia.com/Watkins-Glen-Hotels.d183731.Travel-Guide-Hotels)
- [Hotels in Plattsburgh](https://expedia.com/Plattsburgh-Hotels.d2816.Travel-Guide-Hotels)
- [Hotels in Ithaca](https://expedia.com/Ithaca-Hotels.d6056124.Travel-Guide-Hotels)
- [Hotels in Syracuse](https://expedia.com/Syracuse-Hotels.d601764.Travel-Guide-Hotels)
- [Hotels with a View in Niagara Falls](https://expedia.com/Niagara-Falls-Hotels-Hotels-With-View.0-0-d602721-tHotelswithView.Travel-Guide-Filter-Hotels)
- [Hotels in Binghamton](https://expedia.com/Binghamton-Hotels.d6034018.Travel-Guide-Hotels)
- [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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