Price Vacation Rentals

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Dec 14 - Dec 15
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Dec 15 - Dec 16
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Dec 19 - Dec 21
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Dec 26 - Dec 28

Our top choices for Price vacation rentals

Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Villa in Rock Hall

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Property grounds
First Floor Studio Apartment in Historic Chestertown

Apartment in Chestertown

First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
$144 nightly
The price is $159
Dec 15 - Dec 16
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$262 nightly
The price is $278
Jan 1 - Jan 2, 2026
Total with taxes and fees
BAYSIDE BUNGALOW
Smart TV, fireplace, books
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Cabin in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
10.0 out of 10, Exceptional, (12)
"Great cabin and the dock is amazing. Family and dog had a lot of fun and it was convenient for visiting beaches and parks. "
United States
Marnie D.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

Cass-N-Reel Luxury Houseboat
10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Vacation Home in stevensville

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Private kitchen
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Vacation Home in Chestertown

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
10.0 out of 10, Exceptional, (3)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Property grounds
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Vacation Home in Grasonville

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Interior
200 steps to the beach!

Vacation Home in Rock Hall

200 steps to the beach!
10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Beach
Stay in the landmark Lighthouse!

Vacation Home in Rock Hall

Stay in the landmark Lighthouse!
10.0 out of 10, Exceptional, (107)
"Beautiful home. Wish I could of stayed longer "
United States
Pat R.
Stay in the landmark Lighthouse!
Outdoor dining
Waterfront Paradise on the Eastern Shore of Chesapeake Bay

Vacation Home in Rock Hall

Waterfront Paradise on the Eastern Shore of Chesapeake Bay
10.0 out of 10, Exceptional, (73)
"This trip was a girls get away & we thoroughly enjoyed ourselves .. the house was by far the best I’ve ever rented .. clean, well appointed, & decor was gorgeous … the owner was so attentive & acted on anything we needed right away .. I highly recommend this property & we will definitely be returning …"
United States
Denise O.
Waterfront Paradise on the Eastern Shore of Chesapeake Bay
Beach
Waterfront Retreat with Private Dock and Beach

Apartment in Worton

Waterfront Retreat with Private Dock and Beach
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
$282 nightly
The price is $311
Dec 15 - Dec 16
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Vacation Home in Rock Hall

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
$257 nightly
The price is $272
Dec 15 - Dec 16
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants
Fridge, microwave, dishwasher, coffee/tea maker
Serene Waterfront Cottage with dock and gorgeous views.

Vacation Home in Rock Hall

Serene Waterfront Cottage with dock and gorgeous views.
9.6 out of 10, Exceptional, (38)
"Easy check in and check out. Beautiful water veiw. We really enjoyed having access to the kayaks. The house was just as the listing said it would be. Definitely would rent again. "
United States
Tim S.
Serene Waterfront Cottage with dock and gorgeous views.
Smart TV, fireplace
RELAX- Eastern Shore Creek Home - 6 Guests

Vacation Home in Grasonville

RELAX- Eastern Shore Creek Home - 6 Guests
10.0 out of 10, Exceptional, (5)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests
Outdoor dining
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Vacation Home in Rock Hall

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
10.0 out of 10, Exceptional, (50)
"well supplied, close to the beach, comfortable. our foursome had a great time. "
United States
sarah m.
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Fridge, microwave, oven, stovetop
Waterfront! Private Dock, Boat Tie-Up & Near Town

Vacation Home in Rock Hall

Waterfront! Private Dock, Boat Tie-Up & Near Town
10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town
Exterior
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Vacation Home in Galena

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
9.8 out of 10, Exceptional, (24)
"Wonderful property, well stocked, and great location. Would definitely stay here again!"
United States
Ken K.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
On the beach, beach towels
WATERFRONT right on a BEACH

Vacation Home in Rock Hall

WATERFRONT right on a BEACH
10.0 out of 10, Exceptional, (51)
"Beautiful house and property. Tracy is a very helpful and welcoming host. Will definitely be returning!"
United States
Ryan B.
WATERFRONT right on a BEACH
Game room
Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026

Vacation Home in Centreville

Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026
9.6 out of 10, Exceptional, (35)
"Great location and plenty of fun"
United States
Carl S.
Holiday & Military Bowl Promo: 10% Off Stays through Jan 3, 2026
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 Price Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Everything was well!"
Ahmed 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown

Find out more about Price

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

Price vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Price. 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 Price 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 $159 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 Price rentals

At Expedia, we put the best Price 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 Price 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 Price 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 Price. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Price?

Yes, we give you a choice of vacation rentals close to popular local attractions in Price, or you can select a more remote option if you're looking for relaxation.

What's the top vacation rental in Price?

Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit: Visitors like this Price vacation home rental. It offers a fireplace, a hot tub, and a barbecue grill to help you feel perfectly comfortable 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.

What can I see and do in Price?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Eastern Neck National Wildlife Refuge. River Arts Chestertown and Washington College are a couple of places you'll find in the larger area.

What are vacation rentals like in Price?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Price. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.