Kingston Vacation Rentals from CA $111: Short-Term Rentals for 2025

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

Cottage near the Bay : This vacation home rental near Kingston is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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Vacation Rentals in Kingston

"I like the fact that we were away from the hustle and bustle. The beaches are near by. And it was an overall great experience. Especially if you like secluded areas "

"First time trying this style rental and I’m absolutely happy with the decision. The host was very accommodating and available to answer questions I had plenty of local information on hand to do things very family-friendly fun. "

CA $259 total

includes taxes & fees

Aug 3 - Aug 4

"The Captain’s Roundhouse was a great place to spend a relaxing week. The view is terrific and the kitchen is newly renovated."

CA $1,138 total

includes taxes & fees

Aug 6 - Aug 7

"Wonderful stay excellent area"

"This property was perfectly located in between Chincoteague Island and Janes Island State Park which were both destinations that I wanted to visit on my Spring Break. The property is rural and quiet. "

"We have family in the area and this was our second time staying at Knot Stressed while we visited them. It's the perfect size for our family of 4. It's clean, quiet, and equipped with all the necessities. We loved walking around the neighborhood and out to the water. We'll stay here every time we come to visit."

"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."

CA $650 total

includes taxes & fees

Aug 24 - Aug 25

"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"

"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"

CA $181 total

includes taxes & fees

Aug 5 - Aug 6

"Nice camper in a gated campground. Quiet area. Easy check in. Very helpful with any questions we had."

"Beautiful property"

"Great house. Clean. Had everything we needed."

"very clean and neat, quiet. just what i needed"

"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"

CA $410 total

includes taxes & fees

Aug 3 - Aug 4

"I have to admit, I didn’t want to leave - so I stayed another night.The Barn itself is just absolute perfection…. Not to mention the beyond beautiful setting!I haven’t been that relaxed in years."

"Loft was spotless, and had everything we needed. "

CA $357 total

includes taxes & fees

Aug 6 - Aug 7

"This was our 2nd time staying in this home. It's so spacious and has amazing views. We loved that we were able to bring our dog, as well."

"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "

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Top Kingston Hotel Reviews

Beautiful Bayfront with Sanctuary Private Beach

10/10 Excellent

"The bay is directly in the backyard where you can see the sun set each evening from the house. There is a small beach that is sandy during low tide. If you want to wade in the bay, wear water shoes because there is glass that washes in from the bay. Mosquitoes are a problem, but it isn't just here. That's just the Eastern Shore in summer. If it is windy they aren't too bad if you use bug spray. But we didn't spend much time outside and didn't use the fire pit area, although it looked lovely.The house is as pictured. The king sized bed is a sleep number bed which took some getting used to for us. The bunk beds are double bed sized. The living room had a very comfortable sofa and a table with 6 chairs so there was plenty of room for us. The house could use a few more kitchen items like baking sheets, a pizza cutter, and some more glasses. We didn't try the water and just bought bottled water as advised in the listing.Saxis is peaceful and we enjoyed seeing the wading birds (and one evening a fox!) as we drove past the marsh coming in and out. Chincoteague is about 40 min away but the drive is easy."

Historic home on Smith Island w/ dock!

10/10 Excellent

"The owner and host were Great!! The property was pretty perfect and even nicer than i expected. Getting there was easy from the boat ride to being brought to the property. The Captain of the Jason is right across the street and his wife manages the property. There were 6 of us and from using the bikes, renting a golf cart and walking it was super easy getting around. My brother and I kayaked across to an Island near the inlet with the kayaks on property and it is beautiful there. Looks like great fishing at the right time of year. All the seafood was spot on!!"

Hampton Inn & Suites Salisbury/Fruitland

10/10 Excellent

"We did a lot of traveling on this day and we’re looking forward to our stay at the Hilton. It was perfect! Quiet, clean and friendly staff. We fell asleep immediately! I would recommend staying here to anyone who loves a good quality place to rest and recharge!"

Stunning waterfront panoramic view getaway house

10/10 Excellent

"Property was exceptional. Nick anticipated everything that we might possibly need and provided it to us at check in without us needing to ask. We couldn’t be happier with our stay and will definitely be booking this property again in the future. "

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kingston vacation rentals we have selected for you start as low as CA $111 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 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.

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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?

Cottage near the Bay: This vacation home rental near Kingston is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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 Maddox Island. Pocomoke Fair Grounds and Pocomoke City Hall 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.

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Kingston Vacation Rentals

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Vacation Rentals in Kingston

Cabin at Holdens Creek on Eastern Shore of VA

Cabin at Holdens Creek on Eastern Shore of VA

Cottage near the Bay

Cottage near the Bay

Stunning waterfront panoramic view getaway house

Stunning waterfront panoramic view getaway house

Camping at its best

Camping at its best

Serenity Cottage: Central to state parks, historic towns, MD & VA beaches

Serenity Cottage: Central to state parks, historic towns, MD & VA beaches

Kick back and relax at “Knot Stressed” in total comfort.

Kick back and relax at “Knot Stressed” in total comfort.

The purple door at the bay.

The purple door at the bay.

Beautiful Bayfront with Sanctuary Private Beach

Beautiful Bayfront with Sanctuary Private Beach

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

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

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Vacation camper

Vacation camper

Trails End Campground 20 min-Chincoteague Island 40 min-OCMD 2 hrs-VA Beach

Trails End Campground 20 min-Chincoteague Island 40 min-OCMD 2 hrs-VA Beach

Walk to Main Street: Family-Friendly Crisfield Gem

Walk to Main Street: Family-Friendly Crisfield Gem

Waterfront Historic Gem w/ Kayaks & Fire Pit

Waterfront Historic Gem w/ Kayaks & Fire Pit

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

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

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

The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches

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

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

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Top Kingston Hotel Reviews

Beautiful Bayfront with Sanctuary Private Beach

Find out more about Kingston

Find out more about Kingston

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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