Price Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Price holiday rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"

Charr

HK$1,246 total

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

2. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

HK$981 total

includes taxes & fees

5 Oct - 6 Oct

A kitchen with wooden cabinets, a dining table, and a refrigerator.

3. Family Retreat at Lansdowne Manor

Centreville

Emily C.

A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

4. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

HK$2,150 total

includes taxes & fees

11 Oct - 12 Oct

A modern exterior with a black door, a metal staircase, and a lantern.

5. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

6. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall

lisa p.

HK$2,304 total

includes taxes & fees

4 Oct - 5 Oct

A deck with outdoor furniture, a potted plant, and a house in the background.

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...

Miriam G.

HK$2,420 total

includes taxes & fees

7 Oct - 8 Oct

A modern kitchen with dark cabinets, a white countertop, and a large window.

8. Cass-N-Reel Luxury Houseboat

Grasonville

Danny B.

HK$2,105 total

includes taxes & fees

8 Oct - 9 Oct

A hallway with wooden flooring, a door on the right, and a window at the end.

9. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

HK$3,776 total

includes taxes & fees

27 Oct - 28 Oct

A building with a gabled roof and a circular vent on the roof.

10. BAYSIDE BUNGALOW

Rock Hall

Diane V.

HK$2,477 total

includes taxes & fees

4 Oct - 5 Oct

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

11. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

12. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville

Robin

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

13. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

HK$1,854 total

includes taxes & fees

1 Nov - 2 Nov

A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

14. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

HK$2,477 total

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

15. Turtle Cove Room

Kent County

HK$1,790 total

includes taxes & fees

1 Nov - 2 Nov

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

16. Turnbridge Manor

Denton

Glenn S.

HK$4,782 total

includes taxes & fees

6 Oct - 7 Oct

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Top Price Hotel Reviews

Hilton Garden Inn Kent Island Marina

10/10 Excellent

"Had a good time. Nice area"

Cass-Away Luxury Houseboat

10/10 Excellent

"The place was just as advertised, very clean and comfortable. It's walking distance to good restaurants, bars and entertainment. No issues at all. Unfortunately for us it rained the entire weekend but still plenty to do. Hope to go again and take advantage of the beautiful views from the rooftop deck on the water."

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent

"This is an excellent setting for my wife's 70th birthday, with three children, their spouses/significant others, and four dogs. The owner was congenial and extremely easy to work with and communicate with. The owner does not understate when saying that the house is well-furnished with what one would need for an extended stay, including spices, cooking oil, storage options, etc. The rooms are comfortable and spacious. The porches have beautiful and expansive views of the water, and the beach was so relaxing. the one issue that we had was with the locking mechanism to get in. We are older and our short-term memory is limited. There was a resulting bit of a dance to enter the code in a timely fashion into the lock to open it. It was helpful to have younger people who are digitally quicker. Otherwise, an excellent stay and we look forward to the next time we can stay."

Haven Point Inn and Gallery

8/10 Good

"It was very nice they offered a homecooked breakfast with tea and coffee. However I prefer access to coffee in my room when I want it. No microwave in room, you have to go downstairs to the art gallery to use one. None of the rooms had a long mirror, Parking is a issue, especially if you have a guest come over or stop bye. Or come with more then 1 vehicle. Also would have been nice to have had soda and snack machine since the entire town shuts down early. Overall it was clean, owner was very nice, and id probably stay again."

Find out more about Price

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Frequently asked questions

Are there holiday rentals in Price?

Yes, there are holiday rentals close to the most popular sights in Price, 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 Price has to offer?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This holiday home rental outside of Price is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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. Chestertown Historic District and River Arts Chestertown are a couple of places you'll find in the wider area.

What are holiday rentals like in Price?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Price. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family trips.

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Check prices for these dates

Our top choices for Price holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

2. Guest Suite for up to 2 in a Victorian on the Chester River

3. Family Retreat at Lansdowne Manor

4. Secluded Cottage in Middle of Chestertown

5. Cass-Away Luxury Houseboat

6. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

7. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

8. Cass-N-Reel Luxury Houseboat

9. Wren Retweet- Country Estate in Center of C’Town

10. BAYSIDE BUNGALOW

11. Bayside Cottage steps from Rock Hall Harbor

12. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

13. Beachcomber Suite

14. Waterfront Retreat with Private Dock and Beach

15. Turtle Cove Room

16. Turnbridge Manor

Find holiday rentals that suit your style

Top Price Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hyatt Place Kent Narrows & Marina

Cass-Away Luxury Houseboat

240' Private Beachfront @Kent Island Love Point - Great for Families

The Lodge at Great Oak Landing

Holiday Inn Express Annapolis East-Kent Island by IHG

Serene Waterfront Cottage with dock and gorgeous views.

Haven Point Inn and Gallery

Life is better at the RIVER!--Cozy waterfront cottage

Find out more about Price

Frequently asked questions

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