Crumpton Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Crumpton vacation rentals

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

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (34 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AED 250
AED 428 total
includes taxes & fees
18 Nov - 19 Nov
Guest Suite for up to 2 in a Victorian on the Chester River
A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (35 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is AED 826
AED 1,235 total
includes taxes & fees
16 Nov - 17 Nov
Newly restored apartment in the heart of Chestertown
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (135 reviews)
"Easy to find and good parking. Nice quiet neighborhood. Has refrigerator and microwave. Excellent hot water. Thanks"
United States
Donna G.
The price is AED 364
AED 552 total
includes taxes & fees
16 Nov - 17 Nov
First Floor Studio Apartment in Historic Chestertown
A modern kitchen with stainless steel appliances, a central island, and bar stools.

4. Peaceful Farmhouse Getaway on a Working Farm

Peaceful Farmhouse Getaway on a Working Farm
Kennedyville
The price is AED 767
AED 860 total
includes taxes & fees
16 Nov - 17 Nov
Peaceful Farmhouse Getaway on a Working Farm
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"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...
United States
Miriam G.
The price is AED 727
AED 1,001 total
includes taxes & fees
30 Nov - 1 Dec
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A wooden staircase leading to a beach with a clear view of the sea.

6. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is AED 658
AED 1,258 total
includes taxes & fees
17 Nov - 18 Nov
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

7. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is AED 595
AED 703 total
includes taxes & fees
23 Nov - 24 Nov
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Lisa E.
The price is AED 639
AED 755 total
includes taxes & fees
23 Nov - 24 Nov
Beachcomber Suite
A kitchen with wooden cabinets, a dining table, and a refrigerator.

9. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is AED 900
AED 1,077 total
includes taxes & fees
16 Nov - 17 Nov
Family Retreat at Lansdowne Manor
Restaurant

10. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AED 1,135
AED 1,204 total
includes taxes & fees
16 Nov - 17 Nov
Bohemia Manor Farm
A building with a gabled roof and a circular vent on the roof.

11. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Great hosts… come to Rock Hall every year and found this cute cottage…will def come here every year. Great place"
United States
Nanci H.
The price is AED 735
AED 1,105 total
includes taxes & fees
16 Nov - 17 Nov
BAYSIDE BUNGALOW
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (36 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AED 492
AED 1,072 total
includes taxes & fees
21 Nov - 22 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A modern living room with a flat-screen TV, a brown sofa, a dining table with placemats, wicker chairs, and a kitchen area with a microwave and stove.

13. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
10.0 out of 10, Exceptional, (1 review)
"I was the first guest to stay at the Bohemia Hideaway and I was impressed. The place was spotless and brand new and beautifully decorated. The Owner left a care package filled with toiletries for personal use and every coffee flavor and tea flavor you could imagine. Even little honey packets. The scenery was beautiful. Tucked away and peaceful. Thank you for a wonderful stay."
United States
Isabelle M.
The price is AED 727
AED 804 total
includes taxes & fees
1 Dec - 2 Dec
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
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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Find vacation rentals that suit your style

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Top Crumpton Hotel Reviews

A hotel lobby with a fireplace, seating area, and a television.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Excellent

Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would make a big difference in first impressions!!
United States
Laura
Reviewed April 12, 2025
Comfort Inn & Suites Chestertown

Frequently Asked Questions

Are there vacation rentals in Crumpton?

Yes, we give you a choice of vacation rentals close to popular local attractions in Crumpton, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Crumpton has to offer?

The Colonial Farmhouse with Private Boat Rental: This vacation home near Crumpton offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Crumpton?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Betterton Beach. In the larger area, you’ll find Crow Farm and Vineyard and Rolphs Wharf Marina.

What’s a vacation rental in Crumpton like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Crumpton. Vacation rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of 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 a great option for small groups.