Title: Shelter Island Villas from CA $115 | Expedia.ca

  

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# Search Shelter Island Villa Rentals from CA $115

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## Check prices for these dates

Next weekend

[Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=157359&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Shelter Island Villas

We don't have any properties that match your exact search

[See all properties in Shelter Island](https://expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08&regionId=157359&adults=2)

## Recommended hotels in Shelter Island

![Exterior](https://images.trvl-media.com/lodging/40000000/39940000/39934500/39934446/d21960b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

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

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

### Work and Play Special! Extended Stay Discount

Shelter Island

10/10

Exceptional

(52)

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

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

Nava S.

CA $1,007

CA $1,862 total

includes taxes & fees

Nov 5 - Nov 6

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

![Exterior](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/92c1b984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7bb1af0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free self parking](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/7836a152.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/12000000/11960000/11951300/11951206/f2520f08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Clinton Motel

Clinton

8.6/10

Excellent

(287)

"Great staff and clean rooms"

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

Tyler

CA $109

CA $125 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Old-Saybrook-Hotels-Clinton-Motel.h11951206.Hotel-Information)

![King Ocean Front | Balcony view](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/f520a49e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium King Ocean Front](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/720dfd39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/7a84d66f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool, open 10:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/106000000/105620000/105612600/105612509/bd8b651c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Blue Hotel

Downtown Montauk

9.2/10

Wonderful

(169)

"The beach view is spectacular the surrounding area has everything you need for a each getaway"

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

Jason

CA $166

CA $190 total

includes taxes & fees

Nov 9 - Nov 10

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

![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/afdef753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/31bd2f7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/1000000/20000/12200/12143/72f65e39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

8.0/10

Very good

(1001)

"Staff was incredibly communicative, kind, and patient. Definitely recommend and we would stay again!"

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

Laura

CA $111

CA $128 total

includes taxes & fees

Oct 26 - Oct 27

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

![Exterior](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/a27d78bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/f4e648ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/b026cb5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/2000000/1180000/1177400/1177328/39934cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

7.2/10

Good

(456)

"the so-called breakfast was absolute minimum only thing available was make your own waffle"

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

Brian

CA $100

CA $115 total

includes taxes & fees

Oct 30 - Oct 31

[](https://www.expedia.ca/Old-Saybrook-Hotels-Econo-Lodge-Inn-Suites-Old-Saybrook-Westbrook.h1177328.Hotel-Information)

![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/176892a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/efe89d02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/35541bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/9000000/8480000/8475000/8474914/78e3666a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kenny's Tipperary Inn

Culloden Shores

8.4/10

Very good

(869)

"Love this place. "

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

Susan

CA $162

CA $192 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Montauk-Hotels-Kennys-Tipperary-Inn.h8474914.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/7564e116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/65f0ee8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast area](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/ee8b7737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Reception](https://images.trvl-media.com/lodging/16000000/15250000/15241400/15241380/f90ba663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shorewood Inn

Riverhead

8.6/10

Excellent

(701)

"Bed was very comfortable.. staff was very friendly.. loud traffic in AM.. good water pressure.. would stay here again. "

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

Shelly

CA $130

CA $149 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Riverhead-Hotels-Shorewood-Inn.h15241380.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/8ac37006.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/04aa4e82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/d096a355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1220000/1210400/1210398/e77eab74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hamlet Inn

Southampton

8.6/10

Excellent

(432)

"A solid inexpensive stay in the Hamptons. Staff are very accommodating, they helped guide us when there was an upcoming storm. Room was comfortable and clean. "

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

Michelle

CA $150

CA $194 total

includes taxes & fees

Nov 2 - Nov 3

[](https://www.expedia.ca/Southampton-Hotels-Hamlet-Inn.h1210398.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8d844436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/9aa57818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/8ffa2c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Standard Room, Multiple Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/4000/3988/0b15e4f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Quality Inn Old Saybrook - Westbrook

Old Saybrook

7.8/10

Good

(1002)

"Breakfast was bomb"

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

Jostiena

CA $131

CA $150 total

includes taxes & fees

Nov 2 - Nov 3

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

![Front of property - evening/night](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/96463a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Suite, 2 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/13000000/12700000/12694100/12694044/37cdbc57.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)

### Montauk Manor

Montauk

9.2/10

Wonderful

(1257)

"Beautiful grounds, excellent staff"

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

Jess

CA $212

CA $269 total

includes taxes & fees

Nov 3 - Nov 4

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

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c790caa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![BBQ/picnic area](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/6f247566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/c614d2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Ocean View 2 Queens with Kitchenette | Private kitchen](https://images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/294d9a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Offshore Montauk

Montauk

9.4/10

Exceptional

(62)

"Great place "

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

Kevin

CA $209

CA $399 total

includes taxes & fees

Nov 9 - Nov 10

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

![Exterior detail](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/2bfbb5cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, open 10:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/f19b1dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Room](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/d8c2a23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite | Living room](https://images.trvl-media.com/lodging/8000000/7880000/7874100/7874046/4a933589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Southampton Long Island Hotel

Southampton

8.6/10

Excellent

(201)

"Good location. Nice people!! "

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

Theresa

CA $198

CA $236 total

includes taxes & fees

Nov 23 - Nov 24

[](https://www.expedia.ca/Southampton-Hotels-Southampton-Long-Island-Hotel.h7874046.Hotel-Information)

![Indoor pool, 2 outdoor pools](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/fcfc464f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private beach, beach towels, kayaking, fishing](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/d705542f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/5c314659.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/10000/7000/6970/f58691c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Montauk Yacht Club

Montauk

8.6/10

Excellent

(1005)

"Wonderful hotel and location "

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

FIONA

CA $222

CA $414 total

includes taxes & fees

Nov 10 - Nov 11

[](https://www.expedia.ca/Montauk-Hotels-Gurneys-Star-Island-Resort-Marina.h6970.Hotel-Information)

![Studio Unit Upper Oceanfront 'San Remo'  | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5e6d6769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 1 Bedroom, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/0c1795de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lower 2 Bedroom 2 Bath Corner Oceanfront | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/5d8554d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Suite, 3 Bedrooms, 2 Bathrooms, Ocean View | Living area](https://images.trvl-media.com/lodging/6000000/5240000/5232900/5232838/4119983f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Sea Crest Resort

Amagansett

9.2/10

Wonderful

(497)

"Perfect location!"

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

Bernadette

CA $240

CA $305 total

includes taxes & fees

Nov 9 - Nov 10

[](https://www.expedia.ca/Amagansett-Hotels-Sea-Crest-Resort.h5232838.Hotel-Information)

![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5c728762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/w2880h1079x0y0-f10fe240.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/806c49e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Honeymoon Room, Jetted Tub](https://images.trvl-media.com/lodging/1000000/450000/447900/447803/5fc9f561.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Atlantic Hotel

Southampton

7.2/10

Good

(958)

"Love the area love the room size clean parking was perfect "

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

Sherwood

CA $125

CA $177 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/06a1fe2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/98ce732d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/fc8f49f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/10000000/9390000/9388200/9388116/ae918eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean Vista Resort

Amagansett

9.0/10

Wonderful

(197)

"Such a beautiful place to stay. Pam at the front was so nice and welcoming. The room was clean it was quiet and everyone was friendly. Love that it has a private beach! Would 10/10 recommend it and deff will be going back."

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

kayla c

CA $188

CA $214 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Amagansett-Hotels-Ocean-Vista-Resort.h9388116.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/f08791bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Double Room | Private kitchenette](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/b36c7eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/ff8b5175.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106840000/106830300/106830297/a206dde5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampton Bays Hotel on Main

Hampton Bays

7.0/10

Good

(65)

"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"

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

Olivia

CA $159

CA $182 total

includes taxes & fees

Nov 24 - Nov 25

[](https://www.expedia.ca/Hampton-Bays-Hotels-Hampton-Bays-Hotel-On-Main.h106830297.Hotel-Information)

![Suite, Balcony | View from room](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/48143ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Seasonal outdoor pool](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/c4314d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/84656cf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's play area - outdoor](https://images.trvl-media.com/lodging/10000000/9340000/9337100/9337066/61dd3b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Ocean View Terrace Inn

Hampton Bays

8.4/10

Very good

(119)

"This place was very nice and quiet. "

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

Shelly Ann

CA $201

CA $314 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Hampton-Bays-Hotels-Ocean-View-Terrace-Inn.h9337066.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/5a24caee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/a79f88d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/7abafcfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105960000/105953400/105953388/3da43463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### New and Modern Bridgehampton Accommodations

Bridgehampton

9.6/10

Exceptional

(15)

"Great home, as pictured, perfect place to stay!"

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

Peter R.

CA $245

CA $613 total

includes taxes & fees

Oct 26 - Oct 27

[](https://www.expedia.ca/Bridgehampton-Hotels-New-And-Modern-Bridgehampton-Accommodations.h105953388.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/10f54062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/765aa668.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/b72c2ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114540000/114533200/114533130/f28083b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hidden gem! Southampton beach cottage

Hampton Bays

10/10

Exceptional

(1)

CA $77

CA $639 total

includes taxes & fees

Oct 26 - Oct 27

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

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08&regionId=157359&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true)

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## Top Shelter Island Hotel Reviews

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

### The Sagaponack

10/10 Excellent

"Great place to spend a few days , clean and has everything you need for a comfortable stay ! Located great ! "

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

![Offshore Montauk](//images.trvl-media.com/lodging/114000000/113580000/113578500/113578409/69b11154_y.jpg)

### Offshore Montauk

10/10 Excellent

"Beautifully renovated , super clean property. High quality sheets, towels, very comfortable bed. We enjoyed easy access to the beach and short distance to many dining options. Had wonderful stay and can't wait to come back."

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

![Pier Blue Inn Old Saybrook - Essex](//images.trvl-media.com/lodging/1000000/20000/12200/12143/a912ee6f_y.jpg)

### Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Staff was very helpful and room was nice and clean."

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

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

### The Bentley Hotel Southampton

10/10 Excellent

"It was very spacious!"

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

![Greenporter Hotel](//images.trvl-media.com/lodging/91000000/90310000/90308600/90308554/3c3df51f_y.jpg)

### Greenporter Hotel

10/10 Excellent

"Great location, great service, very clean."

[](https://expedia.ca/Greenport-Hotels-Greenporter-Hotel.h90308554.Hotel-Information)

![Water's Edge Resort & Spa](//images.trvl-media.com/lodging/10000000/9680000/9679900/9679841/3723d6b0_y.jpg)

### Water's Edge Resort & Spa

10/10 Excellent

"We love the stay everything was perfect"

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

![The Atlantic Hotel](//images.trvl-media.com/lodging/1000000/450000/447900/447803/0c137ed2_y.jpg)

### The Atlantic Hotel

10/10 Excellent

"Great stay overall. Only suggestion would be to put a light on the side of the building. "

[](https://expedia.ca/Southampton-Hotels-The-Atlantic-Hotel.h447803.Hotel-Information)

![Marram](//images.trvl-media.com/lodging/16000000/15410000/15408300/15408228/619dc6c0_y.jpg)

### Marram

10/10 Excellent

"We came during terrible weather and couldn’t enjoy the amenities but the view and overall property is beautiful. Johnny at the front desk was very friendly and helpful. "

[](https://expedia.ca/Montauk-Hotels-Marram.h15408228.Hotel-Information)

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

### Saybrook Point Resort & Marina

10/10 Excellent

"Beautiful property, we loved our room, friendly staff. "

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

## Find out more about Shelter Island

## Shelter Island Villas information

| Number of reviews | 9,343 |
| --- | --- |
| Accommodation | 39 Villas |
| Lowest Price | CA $115 |
| Highest Price | CA $1,862 |

## Frequently asked questions

### Why book your villa in Shelter Island with Expedia?

> Reserving a villa in Shelter Island is as easy as working out your travel dates and choosing an option that has what you need. Seeking something luxurious or low cost, or a stay that also includes a kitchen? Use Expedia's search filters to narrow your results and find the ideal fit at the right price.

### How can I find cheap villas in Shelter Island?

> With Expedia's helpful filter tool, locating cheap villas in Shelter Island couldn't be easier. To discover properties that are easy on your bank balance, refine your search by star rating, budget and amenities.

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-   [Flights to Greenport](https://www.expedia.ca/Cheap-Flights-To-Greenport.d110728.Travel-Guide-Flights)
-   [Flights from Southold](https://www.expedia.ca/lp/flights/183719/flights-from-southold)
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-   [Flights from Toronto (YYZ) to New York (NYC)](https://www.expedia.ca/lp/flights/yyz/nyc/toronto-to-new-york)

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-   [Book Villas in Shelter Island on Expedia.com](https://www.expedia.com/Shelter-Island-Villas.d157359-aaVillas.Travel-Guide-Accommodation)