Kingston Holiday Rentals

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Holiday Rentals in Kingston

Coves Point - You can't get more Waterfront than this!

Captain's Cove
9.4 out of 10, Exceptional, (14)
"Best vacation ever, loved fishing on the Bay.. I would certainly go back again !!"
United States
sandesh s.
Coves Point - You can't get more Waterfront than this!

Cabin at Holdens Creek on Eastern Shore of VA

Temperanceville
9.6 out of 10, Exceptional, (180)
"Beautiful place and nice and quiet. We loved it."
United States
Jon L.
Cabin at Holdens Creek on Eastern Shore of VA

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
United States
Bob H.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Anchor's Away - Waterfront, Pet Friendly, Pools!

Captain's Cove
10.0 out of 10, Exceptional, (2)
"The home was lovely, very nicely decorated, beds were very comfortable. "
United States
Jennifer A.
Anchor's Away - Waterfront, Pet Friendly, Pools!

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (50)
"We had a great time! Everything went smoothly from beginning to end! We would definitely stay here again. "
United States
Jennifer J.
The price is NZ$331
includes taxes & fees
15 Nov - 16 Nov
Cottage near the Bay

The purple door at the bay.

Captain's Cove
9.2 out of 10, Wonderful, (54)
"We had a great week staying in Captains Cove. The house met all our needs and the amenities at the marina were wonderful. Only wish would be that the house had wifi."
United States
Katrina S.
The price is NZ$796
includes taxes & fees
17 Nov - 18 Nov
The purple door at the bay.

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Captain's Cove
9.8 out of 10, Exceptional, (59)
"We enjoyed our stay. Our host was very responsive and the community amenities and access to Chincoteague and Assateague are excellent."
United States
Kristen Z.
The price is NZ$819
includes taxes & fees
18 Nov - 19 Nov
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Coastal Crab - Waterfront with incredible Amenities.

Captain's Cove
9.0 out of 10, Wonderful, (4)
"Peaceful cove location, elevator and roomy unit were ideal for a restful week. Could be improved: king bed mattress (hard as a rock, woke up with sore backs every morning); kitchen fruit fly invasion (we battled them all week with our own saucer-vinegar traps); no instructions for door lock that would not lock from the inside/no deadbolt (called prop. mgmt to help secure on our arrival); electric receptacles in master bathroom went out 2 days before our departure (we alerted prop. mgt.); larger...
United States
Audra C.
Coastal Crab - Waterfront with incredible Amenities.

Sun Rayes - Pet friendly; Waterfront w/ Boat dock!

Captain's Cove
8.6 out of 10, Excellent, (48)
"Renting was very easy & laid back. Questions were answered quickly. Contactless check-in was effortless & a timesaver. Loved the property. There was so much space inside & out. Loved the water views!"
United States
David H.
Sun Rayes - Pet friendly; Waterfront w/ Boat dock!

Home in historic Whitehaven Village.

Quantico
10.0 out of 10, Exceptional, (5)
"Great stay! Nice and relaxing and owner fast response with questions!"
United States
susan s.
Home in historic Whitehaven Village.

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Smith Island
10.0 out of 10, Exceptional, (18)
"We just finished a 2 day stay at the Idle Hour and wished we had more time. Our Smith Island stay would not have been the same without Marykim. She helped us with our bags, gave us amazing advice and was a terrific cook and hostess. Would not hesitate to book again."
United States
Anonymous traveller
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Your Song - Gorgeous Waterfront in Captain's Cove!

Captain's Cove
10.0 out of 10, Exceptional, (2)
"This was the best vacation we have ever had. Peaceful. Beautiful. Everything we want in a relaxing trip. Will definitely stay here again!"
United States
Ashley K.
Your Song - Gorgeous Waterfront in Captain's Cove!

Charming bungalow on the bay behind Chincoteague

Horntown
6.0 out of 10, (1)
"Overall, this was a pleasant place to stay for the evening. The community was extremely cute, and we enjoyed walking our dogs around the property. There were a few issues that could easily be fixed. The bathrooms that were closest to the property were locked, and we had trouble finding ones that were open. (We arrived after dark.) Also, because we came in after dark, it was difficult to get into the house. There weren't any lights, and the community is very dark. Adding some sort of small light...
United States
Caroline S.
Charming bungalow on the bay behind Chincoteague

Seahorse Cove - Screened porch, Shared pools!

Captain's Cove
10.0 out of 10, Exceptional, (3)
"I cant say enough about how amazing our stay was. The house was wonderful. I wish we had more household items, like dish detergent, for the length of stay but that wasnt a problem. The community and residents were very friendly. The proximity to Chincoteague is perfect. We stayed an extra day because we didn't want to leave. We are already planning our visit for next year. Thank you! "
United States
Nyoka T.
Seahorse Cove - Screened porch, Shared pools!

Cozy Barn Loft: Country Views & Central to Beaches

Pocomoke City
10.0 out of 10, Exceptional, (19)
"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 NZ$465
includes taxes & fees
15 Nov - 16 Nov
Cozy Barn Loft: Country Views & Central to Beaches

Deal Island Bay Cottage

Deal Island
9.6 out of 10, Exceptional, (57)
"Very nice house and close enough to go places but far enough to be peaceful."
United States
Larry F.
The price is NZ$464
includes taxes & fees
16 Nov - 17 Nov
Deal Island Bay Cottage

Beautiful Bayfront with Sanctuary Private Beach

Saxis
9.2 out of 10, Wonderful, (24)
"We had a wonderful 4 days stay. The location is peaceful and quiet with beautiful views. The house was clean and the host communicated well. Would definetly stay again."
United States
katrina g.
Beautiful Bayfront with Sanctuary Private Beach

Calypso is a breathtaking Waterfront Vacation Home in Captain`s Cove.

Captain's Cove
9.2 out of 10, Wonderful, (35)
"Very spacious and clean beach house with plenty of bathrooms and bedrooms for three generations. Common areas and decks were wonderful!"
United States
Beth M.
Calypso is a breathtaking Waterfront Vacation Home in Captain`s Cove.

Hidden Gem! Clean & Cozy and Family Friendly!

Horntown
9.6 out of 10, Exceptional, (64)
"Very nice house. Wish we were able to stay in a warmer month to check out area."
United States
Jason E.
Hidden Gem! Clean & Cozy and Family Friendly!

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island
9.8 out of 10, Exceptional, (15)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
United States
David
The price is NZ$554
includes taxes & fees
16 Nov - 17 Nov
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart
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

Everything you need to know about Kingston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kingston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kingston holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kingston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kingston holiday rentals we have selected for you start as low as NZ$331 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kingston rentals

At Expedia, we put the best Kingston holiday 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 holiday.

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 holiday rentals in Kingston?

Yes, there are holiday rentals close to the most popular sights in Kingston, or you can select a more secluded option if you're looking for a relaxing stay.

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

Stunning waterfront panoramic view getaway house: This holiday home rental outside of Kingston is located next to a golf course, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. Make the most 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 Fair Grounds and Pocomoke City Hall are a couple of places you'll find in the wider area.

What’s a holiday rental in Kingston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kingston. Holiday rentals offer extras such as WiFi and washers and dryers 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 public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.