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Kingston Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Kingston vacation rentals

A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

1. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
$176 nightly
The price is $187
Oct 19 - Oct 20
Total with taxes and fees
Cottage near the Bay
A sandy beach with footprints, a pier in the distance, and a clear sky.

2. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$232 nightly
The price is $246
Oct 25 - Oct 26
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

3. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
$243 nightly
The price is $257
Oct 20 - Oct 21
Total with taxes and fees
Deal Island Bay Cottage
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

4. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (71 reviews)
"We absolutely love staying here! "
United States
Maggie G.
$409 nightly
The price is $451
Oct 20 - Oct 21
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
A marina at sunset with boats docked and buildings in the background.

5. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (17 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$303 nightly
The price is $334
Oct 19 - Oct 20
Total with taxes and fees
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A sunroom with wicker furniture, large windows, and a view of the water.

6. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 reviews)
"Great location"
United States
Rick K.
$417 nightly
The price is $460
Oct 20 - Oct 21
Total with taxes and fees
The purple door at the bay.
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.
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Top Kingston Hotel Reviews

Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

8/10 Good
"Great customer service and property looked presentable upon arrival. Room was pretty clean but was missed some areas. My concern mainly was the blinds not closing which had me up a lot earlier than I wanted."
Abraham 1-night trip
Posted 7 hours ago
Home2 Suites By Hilton Salisbury Fruitland

Find out more about Kingston

Everything you need to know about Kingston 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 Kingston 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 Kingston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kingston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kingston. 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 Kingston 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 $187 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 Kingston rentals

At Expedia, we put the best Kingston 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 Kingston 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 Kingston 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 Kingston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Kingston?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Kingston, or you can go with a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Kingston has to offer?

Beautiful Bayfront with Sanctuary Private Beach : This vacation home near Kingston offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Kingston?

While exploring the area, visit family-friendly sights like Delmarva Discovery Center, or get outside and enjoy nature at Cypress Park. Pocomoke City Hall and Manokin Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Kingston like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Kingston. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.