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Kingston Vacation Rentals

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Our top choices for Kingston vacation rentals

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
The price is CA $126
CA $279 total
includes taxes & fees
Aug 9 - Aug 10
Cottage near the Bay

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.
The price is CA $223
CA $397 total
includes taxes & fees
Jul 26 - Jul 27
Deal Island Bay Cottage

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.
The price is CA $154
CA $348 total
includes taxes & fees
Jul 26 - Jul 27
Tangier Escape, great place get away from it all on Deal Island, MD.

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
The price is CA $171
CA $380 total
includes taxes & fees
Aug 1 - Aug 2
Pet-friendly Smith Island Cottage w/ Golf Cart!

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.
The price is CA $316
CA $503 total
includes taxes & fees
Jul 25 - Jul 26
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

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.
The price is CA $188
CA $372 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Barn Loft: Country Views & Central to Beaches

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.
The price is CA $291
CA $840 total
includes taxes & fees
Jul 22 - Jul 23
Bayfront Modern Retreat • Dock, Kayaks, Views

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.
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Captain's Cove
The price is CA $461
CA $1,110 total
includes taxes & fees
Jul 26 - Jul 27
Deck & EV Charger: Coastal Retreat 1 Mi to Marina

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.
The price is CA $245
CA $664 total
includes taxes & fees
Aug 8 - Aug 9
The purple door at the bay.

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, (2 reviews)
"My stay was an absolute joy! Very easy to check in and out and the hosts are wonderful! Beautiful outdoor setup! The kids loved it and the beach was a short distance away. Highly recommend!"
United States
Stephanie P.
The price is CA $189
CA $240 total
includes taxes & fees
Aug 4 - Aug 5
Charming camper within Trails End ChinoteagueBay Resort in Horntown VA

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
The price is CA $554
CA $1,084 total
includes taxes & fees
Jul 26 - Jul 27
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

Find out more about Kingston

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kingston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.