Title: Shelter Island Vacation Rentals from $149: 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 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 15 - May 17](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-05-15&endDate=2026-05-17&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jun 12 - Jun 14](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-06-12&endDate=2026-06-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jul 10 - Jul 12](https://www.expedia.com/Hotel-Search?regionId=157359&startDate=2026-07-10&endDate=2026-07-12&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)

![Dining](https://images.trvl-media.com/lodging/91000000/91000000/90991500/90991445/0c11d8f6.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)

### Cottage in Clinton

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

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.

$174 nightly

$197 total

Mar 22 - Mar 23

Total with taxes and fees

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

![Beach nearby](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/2ca462c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/29b6a8ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/7d66373d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106150000/106148000/106147914/77ded06a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Old Lyme

[](https://www.expedia.com/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.Hotel-Information)

10/10

Exceptional

(3 reviews)

"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "

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

Lylian

$195 nightly

$220 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Old-Lyme-Hotels-The-Stern-At-Soundview-BeachOceanViewSunrise.h106147914.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)

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

### Cottage in Greenport

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

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

$224 nightly

$256 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/110000000/109120000/109114300/109114296/878d2c1e.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)

### Vacation Home in East Lyme

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

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.

$311 nightly

$351 total

Mar 22 - Mar 23

Total with taxes and fees

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

![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)

![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)

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

### Cottage in Waterford

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

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.

$268 nightly

$303 total

Mar 22 - Mar 23

Total with taxes and fees

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

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

### Houseboat in Old Lyme

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

$332 nightly

$376 total

Mar 21 - Mar 22

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)

![Exterior](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/d18d0d4f.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)

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

### Aparthotel in Montauk

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

9.2/10

Wonderful

(1,304 reviews)

"Nice pool, great restaurant "

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

April

$168 nightly

$192 total

Apr 6 - Apr 7

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/76a0ec07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/w993h1280x143y0-78873ce1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/4f11d273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/89000000/88740000/88730600/88730550/b4081022.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Hampton North

[](https://www.expedia.com/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.Hotel-Information)

$620 nightly

$660 total

Mar 25 - Mar 26

Total with taxes and fees

[](https://www.expedia.com/East-Hampton-Hotels-Designer-East-Hampton-Farmhouse.h88730550.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)

![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)

### Vacation Home in Waterford

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

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 24 - Mar 25

Total with taxes and fees

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

![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)

![Dining](https://images.trvl-media.com/lodging/106000000/105310000/105302000/105301933/259b8f45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Old Lyme

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

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

$436 nightly

$492 total

Mar 29 - Mar 30

Total with taxes and fees

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

![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/114000000/113310000/113308200/113308197/1f01f033.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)

### Apartment in Clinton

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

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.

$231 nightly

$262 total

Apr 1 - Apr 2

Total with taxes and fees

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

![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)

![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)

### Aparthotel in Napeague

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

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 22 - Mar 23

Total with taxes and fees

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

![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)

![Beach nearby](https://images.trvl-media.com/lodging/11000000/10450000/10449100/10449005/c4e4571c.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)

### Aparthotel in Greenport

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

9.0/10

Wonderful

(249 reviews)

"Great stay - beautiful place"

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

Rebecca

$211 nightly

$241 total

Apr 2 - Apr 3

Total with taxes and fees

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

![Dining](https://images.trvl-media.com/lodging/93000000/92510000/92502500/92502496/41ff71ba.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)

### Vacation Home in Hampton Bays

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

9.6/10

Exceptional

(15 reviews)

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

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

Will K.

$881 nightly

$975 total

Mar 23 - Mar 24

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/93000000/92420000/92415900/92415894/a7c4d35b.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)

### Apartment in East Quogue

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

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

Mar 20 - Mar 21

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/127000000/126440000/126436600/126436578/38483e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436578/d7bdec89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436578/892b2943.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/127000000/126440000/126436600/126436578/feef8da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Westbrook Center

[](https://www.expedia.com/Westbrook-Hotels-1st-Floor-Westbrook-Anchor-2-Queen-Beds-EV-Charger-Near-Beach.h126436578.Hotel-Information)

$315 nightly

$356 total

Mar 24 - Mar 25

Total with taxes and fees

[](https://www.expedia.com/Westbrook-Hotels-1st-Floor-Westbrook-Anchor-2-Queen-Beds-EV-Charger-Near-Beach.h126436578.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)

![Interior](https://images.trvl-media.com/lodging/53000000/52070000/52069800/52069712/6fccc75f.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)

### Vacation Home in Old Lyme

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

9.4/10

Exceptional

(53 reviews)

"Pet friendly, good communication with host, great location and friendly neighborhood. Comfortable cottage. "

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

Ed F.

$249 nightly

$282 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)

![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)

![Interior](https://images.trvl-media.com/lodging/122000000/121400000/121396500/121396426/9036247c.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)

### Vacation Home in Westbrook

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

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.

$470 nightly

$532 total

Mar 24 - Mar 25

Total with taxes and fees

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

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

![Interior](https://images.trvl-media.com/lodging/121000000/120160000/120150900/120150878/89dee084.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)

### Vacation Home in Clinton

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

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.

$236 nightly

$267 total

Mar 21 - Mar 22

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/18f698b7.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)

![Bar (on property)](https://images.trvl-media.com/lodging/72000000/71950000/71943300/71943248/0884fbbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenport

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

9.0/10

Wonderful

(4 reviews)

"We thoroughly enjoyed our stay!"

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

Parent From The Heart, Inc. E.

$229 nightly

$262 total

Mar 22 - Mar 23

Total with taxes and fees

[](https://www.expedia.com/Greenport-Hotels-American-Beech-In-Greenport-Petite-King-Room-7.h71943248.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=2026-04-02&endDate=2026-04-03&regionId=157359&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=APARTMENT)

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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=APART_HOTEL)

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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&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=2026-06-17&d1=2026-06-17&endDate=2026-06-20&d2=2026-06-20&lodging=HOUSE_BOAT)

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## Top Shelter Island Hotel Reviews

![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

4/10 Poor

"My second stay but big disappointment the pool and hot tub wasn’t available for hotel guests this is the second time for me last year same thing happened they closed the spa area there was only pool opened, our room didn’t have any coffee cups no wine glass no any other glass wear, the bathroom need some attention leaking sink and we found many ants in the room "

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

"By far one of the best hotels I’ve ever stayed at. The bed was heaven, the room was huge and decorated so well! "

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

"We loved our stay here. The staff was so wonderful! (Mary Luz at the Starbucks was so sweet!) and the food was fresh and delicious. The waitstaff was attentive and cognizant and caring regarding food allergies. The views from every vantage were special and memorable. We had not great weather and it did not matter!! It was a perfect getaway spot. "

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

![Journey East Hampton](https://images.trvl-media.com/lodging/24000000/23260000/23252100/23252049/52063f27_y.jpg)

### Journey East Hampton

10/10 Excellent

"The Journey is always pleasant. Only issue I have regards buisness travelers....no desk in the rooms."

[](https://expedia.com/East-Hampton-Hotels-Journey-East-Hampton.h23252049.Hotel-Information)

![Saybrook Point Resort & Marina](https://images.trvl-media.com/lodging/1000000/40000/38800/38715/fce2d4ec_y.jpg)

### Saybrook Point Resort & Marina

10/10 Excellent

"Our group of 6 girlfriends had an amazing stay at Saybrook Point Resort & Marina. From the moment we arrived, we knew the weekend was going to be very special. The staff was always warm & welcoming. Shoutout to Scott at reception for ensuring a perfect stay! Dinner at Fresh Salt was delicious & the atmosphere was lively. Shuttle into town was a great option. Can’t wait to book another visit!"

[](https://expedia.com/Old-Saybrook-Hotels-Saybrook-Point-Resort-Marina.h38715.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

6/10 Okay

"My only complaint is the very dim lighting and lack of lighting in the entranceway especially. Otherwise very comfortable and clean."

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

![Hyatt Place Long Island East End](https://images.trvl-media.com/lodging/5000000/4260000/4258100/4258052/df127760_y.jpg)

### Hyatt Place Long Island East End

10/10 Excellent

"Great hotel, clean, walkable area "

[](https://expedia.com/Riverhead-Hotels-Hyatt-Place-Long-Island-East-End.h4258052.Hotel-Information)

![The Harbor Front Inn](https://images.trvl-media.com/lodging/44000000/43540000/43532300/43532300/2c9cc7e9_y.jpg)

### The Harbor Front Inn

10/10 Excellent

"Everything was great! Loved the continental breakfast. "

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

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

### Montauk Manor

10/10 Excellent

"Amazing!"

[](https://expedia.com/Montauk-Hotels-Montauk-Manor.h12694044.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 $149 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
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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)
- [B&B in Shelter Island ](https://expedia.com/Shelter-Island-Bed-And-Breakfast.d157359-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Villas in Shelter Island ](https://expedia.com/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation)
- [Motels in Shelter Island ](https://expedia.com/Shelter-Island-Motels.d157359-aaMotels.Travel-Guide-Accommodation)
- [RV Parks in Shelter Island ](https://expedia.com/Shelter-Island-RV-Parks.d157359-aaRVParks.Travel-Guide-Accommodation)
- [Resorts in Shelter Island ](https://expedia.com/Shelter-Island-Resorts.d157359-aaResorts.Travel-Guide-Accommodation)
- [Farmstay in Shelter Island ](https://expedia.com/Shelter-Island-Agritourism.d157359-aaAgritourism.Travel-Guide-Accommodation)
- [Aparthotels in Shelter Island ](https://expedia.com/Shelter-Island-Apart-Hotels.d157359-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Shelter Island ](https://expedia.com/Shelter-Island-Inns.d157359-aaInns.Travel-Guide-Accommodation)
- [Guest Houses in Shelter Island ](https://expedia.com/Shelter-Island-Guest-Houses.d157359-aaGuestHouses.Travel-Guide-Accommodation)
- [Houseboats in Shelter Island ](https://expedia.com/Shelter-Island-Houseboats.d157359-aaHouseboats.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)
- [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 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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