Shelter Island Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Shelter Island holiday rentals

A kitchen with white cabinets, a central island with stools, a microwave, a stove, and a large window.

1. Work and Play Special! Extended Stay Discount

Shelter Island

Kathleen Andrews K.

HK$10,438 total

includes taxes & fees

15 Sept - 16 Sept

A campsite with several tents and a picnic table.

2. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

East Hampton

Vasilios

HK$2,553 total

includes taxes & fees

20 Sept - 21 Sept

A modern house with a deck, outdoor seating, and a fire pit.

3. North Fork Resort

Greenport

Lisa

HK$2,879 total

includes taxes & fees

14 Sept - 15 Sept

4. Cliffside Resort Condominiums

Greenport

Christine

HK$3,288 total

includes taxes & fees

5 Oct - 6 Oct

A wooden pathway leading to a beach with scattered rocks and greenery.

5. Beach Block Hideaway

Pipes Cove

Teresa C.

HK$3,279 total

includes taxes & fees

14 Sept - 15 Sept

A beach with people relaxing under umbrellas, a dock extending into the water, and a forested hill in the background.

6. Aqua Vista

Pipes Cove

Kerri L.

HK$2,509 total

includes taxes & fees

7 Oct - 8 Oct

A beach with people relaxing on chairs and sunbathing.

7. Harbor Heights

Pipes Cove

Steven R.

HK$2,500 total

includes taxes & fees

5 Oct - 6 Oct

A beach with people relaxing, a pier extending into the water, and a clear sky.

8. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

Pipes Cove

Callie E.

HK$3,185 total

includes taxes & fees

15 Sept - 16 Sept

A beach with people sunbathing, a pier extending into the water, and a clear blue sky.

9. The SandPiper

Pipes Cove

Julian V.

HK$2,948 total

includes taxes & fees

28 Sept - 29 Sept

An outdoor dining area with hanging lights, palm trees, and a bar.

10. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

HK$2,805 total

includes taxes & fees

16 Sept - 17 Sept

11. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

East Hampton

Christina V.

HK$2,553 total

includes taxes & fees

20 Sept - 21 Sept

A dining area with a round table, six chairs, and a chandelier.

12. BlackBerry Private home with jacuzzi yearlong

East Hampton

Suzanne R.

HK$10,122 total

includes taxes & fees

14 Sept - 15 Sept

A campsite with several tents set up among trees.

13. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

East Hampton

Brian F.

HK$2,651 total

includes taxes & fees

18 Sept - 19 Sept

14. Safari Tent Glamping,S6-CedarPt, East Hampton, NY

East Hampton

Lorraine

HK$2,553 total

includes taxes & fees

20 Sept - 21 Sept

15. Safari Tent Glamping,D26-CedarPt, East Hampton, NY

East Hampton

Melissa

HK$2,643 total

includes taxes & fees

17 Sept - 18 Sept

A living room with a fireplace, a television mounted above it, a dining area with a table and chairs, and a staircase with wooden railings.

16. Renovated Townhouse walk to all

Greenport

Melissa A.

HK$5,327 total

includes taxes & fees

17 Sept - 18 Sept

17. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

East Hampton

Fiona B.

HK$2,643 total

includes taxes & fees

17 Sept - 18 Sept

A campground with several tents and trees, a grassy area, and a view of the water.

18. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

East Hampton

Michael H.

HK$2,553 total

includes taxes & fees

18 Sept - 19 Sept

A small cabin with a porch, surrounded by trees and a fenced area.

19. Lovely studio with AC in charming Sag Harbor

Sag Harbor

"For a last minute trip, we couldn't beat the location. Less than 10 minutes from Sag Harbor and Bridgehampton main streets as well as from Sagaponack beaches. The space is quaint and offers everything you need, a small kitchenette, a work desk, outdoor space. There was several communications sent regarding privacy and not interacting with other guests on property which I can appreciate but felt excessive.My two biggest complaints and likely why I would not rebook was first the cleanliness of the...

Emily t.

HK$4,113 total

includes taxes & fees

14 Sept - 15 Sept

A modern dining area with a wooden table, white chairs, and a chandelier.

20. Northfork Townhouse walk to all

Greenport

Beth R.

HK$6,680 total

includes taxes & fees

14 Sept - 15 Sept

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Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

8/10 Good

"The hotel is modest and older but clean. They are working on improving their facilities which is good. Nice staff. We really found the shower pressure to be the best we ever have experienced."

Saybrook Point Resort & Marina

10/10 Excellent

"Gorgeous Inn. Excellent experience overall. Need less puffy pillows on beds…bring your own! All 6 adults in our party were uncomfortable with pillows and slept poorly. Celebrating my husband’s 70th and I checked in earlier with staff to be sure they had the cake (as requested I do) and asked if we could have a particular table (or have a choice). We had 6 adults and one high chair. We were told they only had one table that would accommodate our “large” group. The table we were given was just okay…meanwhile there were groups our size and larger being accommodated at other tables. I was really disappointed about that. One final note…it would be nice to have different menus at the bar vs restaurant. Also if you’re staying out of season and plan to use the indoor pool, the room is extremely hot and humid and barely tolerable due to the chemicals. Otherwise staff was delightful, rooms and common areas beautiful!"

The Atlantic Hotel

8/10 Good

"This property is a lovely option if you want to be near to central Southampton but not in the middle of it. the room was really nicely appointed, they have a lovely grounds area near the pool, and a really nice pool deck with a pretty big heated pool. We really enjoyed the pool. Only negative is that It's located on a 2 lane highway without much close buy in the way of restaurants or other necessities; getting around was awkward and costly without a car. However, the place we stayed at was nice!"

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

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Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best holiday rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This holiday home rental outside of Shelter Island is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many holiday rentals are there in Shelter Island?

Choose from 86 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Mashomack Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Shelter Island Historical Society and Crescent Beach are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.

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Check prices for these dates

Our top choices for Shelter Island holiday rentals

1. Work and Play Special! Extended Stay Discount

2. Safari Tent Glamping,S7-CedarPt, East Hampton, NY

3. North Fork Resort

4. Cliffside Resort Condominiums

5. Beach Block Hideaway

6. Aqua Vista

7. Harbor Heights

8. Blue Bay Dream w/ Seasonal Outdoor Jacuzzi, Cabana + Office

9. The SandPiper

10. American Beech in Greenport - Petite King Room 7

11. Safari Tent Glamping,S10-CedarPt, East Hampton, NY

12. BlackBerry Private home with jacuzzi yearlong

13. Safari Tent Glamping,D28-CedarPt, East Hampton, NY

14. Safari Tent Glamping,S6-CedarPt, East Hampton, NY

15. Safari Tent Glamping,D26-CedarPt, East Hampton, NY

16. Renovated Townhouse walk to all

17. Safari Tent Glamping,D27-CedarPt, East Hampton, NY

18. Safari Tent Glamping,S2-CedarPt, East Hampton, NY

19. Lovely studio with AC in charming Sag Harbor

20. Northfork Townhouse walk to all

Find holiday rentals that suit your style

Top Shelter Island Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Saybrook Point Resort & Marina

Montauk Blue Hotel

Water's Edge Resort & Spa

Kenny's Tipperary Inn

Ocean Resort Inn

The Atlantic Hotel

Gurney's Montauk Resort & Seawater Spa

Offshore Montauk

Find out more about Shelter Island

Frequently asked questions

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