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Crumpton Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Crumpton vacation rentals

Exterior

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, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,726
￥19,730 total
includes taxes & fees
Aug 10 - Aug 11
Guest Suite for up to 2 in a Victorian on the Chester River
Interior

2. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 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 ￥53,292
￥67,009 total
includes taxes & fees
Sep 2 - Sep 3
Family Retreat at Lansdowne Manor
Smart TV, books

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (31 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveler
The price is ￥39,435
￥60,425 total
includes taxes & fees
Aug 20 - Aug 21
Newly restored apartment in the heart of Chestertown
TV, fireplace

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 ￥28,961
￥44,388 total
includes taxes & fees
Aug 19 - Aug 20
Secluded Cottage in Middle of Chestertown
Property grounds

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, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥57,411
￥87,091 total
includes taxes & fees
Aug 17 - Aug 18
Wren Retweet- Country Estate in Center of C’Town
Property grounds

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (119 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is ￥15,616
￥25,055 total
includes taxes & fees
Aug 10 - Aug 11
First Floor Studio Apartment in Historic Chestertown
Property grounds

7. 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 ￥25,160
￥30,936 total
includes taxes & fees
Aug 10 - Aug 11
Beachcomber Suite
1 bedroom, WiFi, bed sheets

8. Turtle Cove Room

Turtle Cove Room
Kent County
The price is ￥22,147
￥27,483 total
includes taxes & fees
Aug 10 - Aug 11
Turtle Cove Room
Beach nearby

9. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is ￥35,492
￥59,718 total
includes taxes & fees
Aug 30 - Aug 31
Waterfront Retreat with Private Dock and Beach
Beach

10. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥19,560
￥46,489 total
includes taxes & fees
Aug 10 - Aug 11
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

11. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥27,605
￥57,352 total
includes taxes & fees
Aug 10 - Aug 11
Bayside Cottage steps from Rock Hall Harbor
Exterior detail

12. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (61 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥28,393
￥43,807 total
includes taxes & fees
Aug 18 - Aug 19
BAYSIDE BUNGALOW
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"Hotel was fine. Area was a little sketchy."
Angelo 1-night trip
Posted 3 hours ago
Comfort Inn & Suites Chestertown

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?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: This vacation home rental near Crumpton is located near the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.