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Crumpton Vacation Rentals

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Check prices for these dates

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

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, (32 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is ￥10,777
￥18,479 total
includes taxes & fees
Nov 10 - Nov 11
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, (34 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 ￥35,658
￥53,287 total
includes taxes & fees
Nov 10 - Nov 11
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
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is ￥15,690
￥23,830 total
includes taxes & fees
Nov 10 - Nov 11
First Floor Studio Apartment in Historic Chestertown
A garden with a wooden bridge, lush greenery, and a variety of plants.

4. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is ￥29,097
￥43,420 total
includes taxes & fees
Nov 10 - Nov 11
Secluded Cottage in Middle of Chestertown
A covered porch with a wooden bench, potted plants, and a decorative railing.

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

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (76 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥48,267
￥72,408 total
includes taxes & fees
Nov 10 - Nov 11
Wren Retweet- Country Estate in Center of C’Town
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

6. 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 ￥31,379
￥43,845 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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 ￥25,674
￥30,336 total
includes taxes & fees
Nov 23 - Nov 24
Turtle Cove Room
A wooden staircase leading to a beach with a clear view of the sea.

8. 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 ￥28,241
￥55,137 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

9. 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 ￥27,576
￥31,738 total
includes taxes & fees
Nov 23 - Nov 24
Beachcomber Suite
A kitchen with wooden cabinets, a dining table, and a refrigerator.

10. 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 ￥37,940
￥45,473 total
includes taxes & fees
Nov 10 - Nov 11
Family Retreat at Lansdowne Manor
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)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,696
￥47,674 total
includes taxes & fees
Nov 10 - Nov 11
BAYSIDE BUNGALOW
Restaurant

12. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is ￥83,761
￥88,787 total
includes taxes & fees
Nov 19 - Nov 20
Bohemia Manor Farm
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

13. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥21,224
￥44,422 total
includes taxes & fees
Nov 12 - Nov 13
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.

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

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
The price is ￥39,937
￥43,794 total
includes taxes & fees
Nov 15 - Nov 16
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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Top Crumpton Hotel Reviews

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

10/10 Excellent
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."
William 2-night trip
Posted 9 hours ago
The Lodge at Great Oak Landing

Find out more about Crumpton

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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.