Shelter Island Vacation Rentals from $173: Search Short-Term Rentals

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Our top choices for Shelter Island vacation rentals

1. Work and Play Special! Extended Stay Discount

Shelter Island

Kathleen Andrews K.

$1,165 nightly

Sep 15 - Sep 16

Total with taxes and fees

2. North Fork Resort

Greenport

Lisa

$275 nightly

Sep 13 - Sep 14

Total with taxes and fees

3. Cliffside Resort Condominiums

Greenport

Christine

$370 nightly

Sep 30 - Oct 1

Total with taxes and fees

4. Beach Block Hideaway

Pipes Cove

Teresa C.

$366 nightly

Sep 14 - Sep 15

Total with taxes and fees

5. The SandPiper

Pipes Cove

Timothy

$329 nightly

Sep 28 - Sep 29

Total with taxes and fees

6. American Beech in Greenport - Petite King Room 7

Greenport

Paul F.

$313 nightly

Sep 16 - Sep 17

Total with taxes and fees

7. Harbor Heights

Pipes Cove

Nigel

$279 nightly

Oct 5 - Oct 6

Total with taxes and fees

8. Aqua Vista

Pipes Cove

Kerri L.

$280 nightly

Oct 7 - Oct 8

Total with taxes and fees

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Top Shelter Island Hotel Reviews

Montauk Blue Hotel

10/10 Excellent

"Front desk staff was extremely knowledgeable, friendly and accommodating. The beach crew was excellent too. They set up and brought back all the necessities so all you had to do was relax."

The Hampton Maid

10/10 Excellent

"Our stay at The Hampton Maid was such a great choice. The entire hotel is absolutely charming—you can tell that every corner and every detail has been thoughtfully designed. The front desk staff was wonderful: so friendly, welcoming, and very clear with all the information. We loved the bungalow-style rooms, each with its own deck and parking, which gives you wonderful privacy between rooms. But what truly stole our hearts was the gorgeous, beautifully kept garden—a true green oasis that brings complete peace and lets you fully disconnect from city stress. The room was spotless, and the restaurant was phenomenal—we had breakfast there, and it was spectacular. On top of that, getting a pass to 7 local beaches for just $5 is an incredible perk. You really couldn't ask for more! It’s one of those places where you haven't even left yet, and you're already planning your return. Can't wait to go back!"

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent

"Welcoming, helpful, friendly, professional front desk staff. My room was impeccably clean and tidy. The property is centrally-located with ease of accessibility to main roads and major highways, yet far enough off Boston Post Road to ensure a quiet, peaceful and restful stay. Overall, an outstanding, no-frills property! I look forward to staying here once again!"

Saybrook Point Resort & Marina

10/10 Excellent

"Old Saybrook never disappoints. The rooms have been remodel Edinburgh the last six months but the resort has managed to retain its old world chatm. Eventhough there were three weddings at the property during our visit, the staff were attentive to us and we weren't as re remained their only guests. We will visit again."

Faraway Sag Harbor

8/10 Good

"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."

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 $173 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.

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Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to 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 vacation home rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Shelter Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 vacation rentals are there in Shelter Island?

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

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 vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.

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Check prices for these dates

Our top choices for Shelter Island vacation rentals

1. Work and Play Special! Extended Stay Discount

2. North Fork Resort

3. Cliffside Resort Condominiums

4. Beach Block Hideaway

5. The SandPiper

6. American Beech in Greenport - Petite King Room 7

7. Harbor Heights

8. Aqua Vista

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

10. Northfork Townhouse walk to all

11. The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

12. Beachfront Greenport Villa

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

14. Renovated Townhouse walk to all

15. Perfection in Sag Harbor : 5 Bedrooms with saltwater pool - walk to Beach

16. Safari Tent Glamping,S4-CedarPt, East Hampton, NY

17. Charming Accommodations in the Hamptons

18. Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

19. Spacious & Modern 5-bedroom in Sag Harbor, walk to bay

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

Find vacation rentals that suit your style

Top Shelter Island Hotel Reviews

Montauk Blue Hotel

Gurney's Montauk Resort & Seawater Spa

Montauk Manor

The Hampton Maid

Pier Blue Inn Old Saybrook - Essex

Saybrook Point Resort & Marina

Faraway Sag Harbor

Find out more about Shelter Island

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