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Kingston Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Kingston vacation rentals

Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (58 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
$178 nightly
The price is $189
Jul 26 - Jul 27
Total with taxes and fees
Cottage near the Bay
Coffee/tea maker, fridge, microwave, oven

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (60 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$246 nightly
The price is $261
Jul 23 - Jul 24
Total with taxes and fees
Deal Island Bay Cottage
Beach

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, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$232 nightly
The price is $246
Jul 25 - Jul 26
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
Cottage (2 Bedrooms) | Interior

Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
$244 nightly
The price is $271
Aug 1 - Aug 2
Total with taxes and fees
Pet-friendly Smith Island Cottage w/ Golf Cart!
Marina

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$326 nightly
The price is $360
Jul 19 - Jul 20
Total with taxes and fees
Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Coffee/tea maker, fridge, microwave, oven

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (21 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
$239 nightly
The price is $268
Jul 21 - Jul 22
Total with taxes and fees
Cozy Barn Loft: Country Views & Central to Beaches
Smart TV, books, offices

Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (66 reviews)
"We absolutely love staying here! "
United States
Maggie G.
$550 nightly
The price is $607
Jul 22 - Jul 23
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
Exterior

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell
10.0 out of 10, Exceptional, (22 reviews)
"Enjoyed Smith Island , great place to stay, friendly people, loved the golf cart a real plus! Flies and mosquitoes were terrible, restaurant food was just OK! Make sure you get food and supplies before coming! "
United States
richard a. g.
$248 nightly
The price is $274
Aug 1 - Aug 2
Total with taxes and fees
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Pool

Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Captain's Cove
$718 nightly
The price is $792
Jul 26 - Jul 27
Total with taxes and fees
Deck & EV Charger: Coastal Retreat 1 Mi to Marina
TV, DVD player

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (62 reviews)
"This is a great property with a great view of the bay. It's tucked away in a quiet little neighborhood in a nice and friendly community. Chincoteague is close by and it's not too far from Assateague. The property management team is excellent. They were extremely responsive to our questions and requests. They were patient with all our questions. Kelly was fantastic. The best hosts I've had."
United States
A Shabeen J.
$409 nightly
The price is $451
Aug 8 - Aug 9
Total with taxes and fees
The purple door at the bay.
Outdoor pool

Charming camper within Trails End ChinoteagueBay Resort in Horntown VA

Charming camper within Trails End ChinoteagueBay Resort in Horntown VA
Horntown
10.0 out of 10, Exceptional, (1 review)
"Such a beautiful space! Relaxing, clean, and spacious! Would love to stay again. Wonderful owners!"
United States
Kristine S.
$145 nightly
The price is $160
Aug 4 - Aug 5
Total with taxes and fees
Charming camper within Trails End ChinoteagueBay Resort in Horntown VA
House (4 Bedrooms) | Interior

Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
3.0 star property
Captain's Cove
$701 nightly
The price is $773
Jul 26 - Jul 27
Total with taxes and fees
Deck & EV Charger: Coastal Retreat 1 Mi to Marina
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

Econo Lodge Princess Anne

Econo Lodge Princess Anne

10/10 Excellent
"Ok"
Taylor 1-night trip
Posted 18 hours ago
Econo Lodge Princess Anne

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 $189 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?

Hidden Gem! Clean & Cozy and Family Friendly!: This vacation home rental near Kingston is located near the beach and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Wellington Beach and 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.