Pine Top Vacation Rentals from $323: Search Short-Term Rentals

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

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE : This vacation home near Pine Top offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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In two weeks

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Our top choices for Pine Top vacation rentals

Luxury Studio Guesthouse, Walk to Museum, Boat Parking

Deltaville

Stan R.

$327 nightly

Jul 19 - Jul 20

Total with taxes and fees

Affordable Cottage!

Deltaville

Jessica T.

$308 nightly

Jul 20 - Jul 21

Total with taxes and fees

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

Diggs

$40 nightly

Jul 16 - Jul 17

Total with taxes and fees

Restored 1920's Cottage on 1 Acre w/ Fire Pit

Hayes

Daniela R.

$290 nightly

Jul 16 - Jul 17

Total with taxes and fees

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

Mathews

Casey J.

$374 nightly

Jul 28 - Jul 29

Total with taxes and fees

Desk, iron/ironing board, free WiFi, bed sheets

Belle Haven - High Speed internet, walk to town

Kilmarnock

Darren W.

$301 nightly

Jul 28 - Jul 29

Total with taxes and fees

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~

Kilmarnock

Melinda H.

$377 nightly

Aug 3 - Aug 4

Total with taxes and fees

The Nook in Kilmarnock Va 3 bedroom

Kilmarnock

Anonymous traveler

$427 nightly

Aug 4 - Aug 5

Total with taxes and fees

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Top Pine Top Hotel Reviews

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

10/10 Excellent

"Great hosts and very helpfull. Unfortunately for us, the majority of our time was spent on Gwynns Island while there. Very easy access to all Matthews county has to offer from this location. Highly recommend this property for longer stays."

Warner Hall

10/10 Excellent

"From the immaculate grounds, to the unreal US history from the Warner family, this destination is a true gem. Phil and Laura; the inn keepers hosted our amazing stay and provided information on the rich history of the site. Austin’s is a wonderful high quality dining establishment on premises with outstanding cuisine, quiet atmosphere, and wonderful wine recommendations by Christian; a top-notch waiter and sommelier. The original house was remodeled to provide outstanding comfort and amenities. The soap, shampoo, and lotion scent is wonderful and unique. This location is a stones throw from Yorktown and other US history. Thank you for a memorable stay. We will be coming back to experience the other rooms and what the Inn has to offer for the things we were not able to get to during this trip!"

Holiday Inn Express Gloucester by IHG

10/10 Excellent

"The property has a great all inclusive breakfast and also love the fact that they have an outdoor pool since the neighboring hotel doesn't. I've stayed here in the past when visiting family near by and haven't been disappointed. Also I want to thank the two front desk employees Michelle and Tyrese, for understanding my situation and being super accommodating to my needs. You guys rock!!! See you all again in the near future."

The Little Blue Cottage - Topping : Waterfront!

8/10 Good

"The floors were dirty in the way that you couldn’t see dirt, but if you walked barefoot you could feel it was gritty and it made our feet dirty. One evening we looked out the window and a man was just outside changing the filter on the water filtration system. It was getting dark and it was alarming to see a strange man in the yard. There were cameras in the carport and on the back of the house that could presumably see through the windows of the house. This felt like a major lack of privacy. The beach down the road had signs that said ‘locals only’ which felt hostile. We were strictly instructed not to step to the right of the driveway which is the exact property line because the neighbors would be upset. This felt uncomfortable. We had a nice time on our trip and made use of the kayaks but the rack holding the kayaks was unstable and fell over when my husband took the kayaks down to use."

Cottage on a Private Island in the York River

10/10 Excellent

"This house is quirky and wonderful. We loved the old part of the house, complete with a small boat in the living room ceiling! Wonderful things to look at all over the house. The new part of the house has large windows and doors for viewing the York River as the tide ebbs and flows. We loved watching the birds fish for their dinner. We had a snowy egret and a blue heron as well as many other birds. The crabs were fun to watch pop in and out of their tunnels. The kitchen has every appliance and pot or pan you could possibly need. Beds were comfy, and fans kept the air circulating. AC worked well, too. Was very close to all the local sights."

Find out more about Pine Top

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

Pine Top vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Top. 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 Pine Top 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 $323 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 Pine Top rentals

At Expedia, we put the best Pine Top 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 Pine Top 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 Pine Top 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 Pine Top. 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 Pine Top?

Yes, we have vacation rentals in Pine Top near Deltaville Maritime Museum, 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 Pine Top has to offer?

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE: This vacation home near Pine Top offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Pine Top?

With 26 Expedia vacation rentals, you're sure to find just the right place for your Pine Top stay.

What’s there to see and do in Pine Top?

Holly Point Nature Park and Chesapeake Bay are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Deltaville Maritime Museum. While here, Deltaville Marina and Regent Point Marina are other places worth a visit.

What’s a vacation rental in Pine Top like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Pine Top. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for small groups.

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Check prices for these dates

Our top choices for Pine Top vacation rentals

Luxury Studio Guesthouse, Walk to Museum, Boat Parking

Affordable Cottage!

RV Site On Blanchard Farm -MAX RV LENGTH 24 FT

Restored 1920's Cottage on 1 Acre w/ Fire Pit

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

Belle Haven - High Speed internet, walk to town

Nearby Beach~HotTub~Pooltable~MovieScreen~NrbyShoppingDiningGoCarts~

The Nook in Kilmarnock Va 3 bedroom

Campsite #4 At Blanchard Farm

Campsite #3 At Blanchard Farm

Charming 3-bedroom villa with WiFi, and Jaccuzzi , just Minutes from Yorktown

Restored 1920's Cottage on 1 Acre w/ Fire Pit

Family Friendly Waterfront Home - Private Dock, Kayaks, Fire Pit, Grill, Deck

Find vacation rentals that suit your style

Top Pine Top Hotel Reviews

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Room on river with sunset views and private beach!

Warner Hall

Hampton Inn Gloucester

Holiday Inn Express Gloucester by IHG

The Little Blue Cottage - Topping : Waterfront!

Cottage on a Private Island in the York River

Dockside Inn

Bethpage Camp-Resort

Find out more about Pine Top

Frequently asked questions

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