Book Holiday Homes in Crumpton

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Featured Holiday Homes in Crumpton

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
The price is AU$451 per night from 27 Oct to 28 Oct
AU$451
27 Oct - 28 Oct
includes taxes & fees
Located in Rock Hall, this vacation home is within a 15-minute walk of Ferry Park and Waterman’s Museum.
Opens in a new windowBAYSIDE BUNGALOW
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown
A stay at this vacation home places you in the heart of Chestertown, steps from Historical Society of Kent County Maryland and Chestertown Historic ...
Opens in a new windowCirca 1900 Home in the Heart of Historic Downtown Chestertown
Entire Townhouse in Rock Hall

Entire Townhouse in Rock Hall

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 15-minute walk of Rock Hall Harbor and The Mainstay.
Opens in a new windowEntire Townhouse in Rock Hall
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Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Middletown
With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of Middletown Historic District and The Everett Annex.
Opens in a new windowSpacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Millington
Located in Millington, this vacation home is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.
Opens in a new windowLark's Nest on the Chester River. Spacious, waterfront home with private dock.
200 steps to the beach!

200 steps to the beach!

Rock Hall
With a stay at this vacation home in Rock Hall, you'll be a 2-minute walk from Ferry Park and 11 minutes by foot from Waterman’s Museum.
Opens in a new window200 steps to the beach!
Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler

Rock Hall
When you stay at this vacation home in Rock Hall, you'll be on the waterfront, within a 5-minute drive of Ferry Park and Waterman’s Museum.
Opens in a new windowStunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Rock Hall
With a stay at this vacation home, you'll be centrally located in Rock Hall, just a 3-minute walk from Waterman’s Museum and 10 minutes by foot from Rock Hall ...
Opens in a new windowSpacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11
Waterfront Lodge packed with Amenities

Waterfront Lodge packed with Amenities

Earleville
Located in Earleville, this vacation home is on the waterfront, a 4-minute drive from Earleville Wildlife Management Area and 9 minutes from Long Point ...
Opens in a new windowWaterfront Lodge packed with Amenities
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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.

Crumpton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Crumpton vacation homes are the perfect way for you to wing it.

Holiday houses in Crumpton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Crumpton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Crumpton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Crumpton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Crumpton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Crumpton Holiday Homes essential information

Accommodation
92 Holiday Homes
Lowest Price
AU$137
Highest Price
AU$451
Popular accommodation
BAYSIDE BUNGALOW, Circa 1900 Home in the Heart of Historic Downtown Chestertown, Entire Townhouse in Rock Hall, Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., 200 steps to the beach!, Stunning Waterfront Home, long pier, pool, featured in Conde Nast Traveler, Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11, Waterfront Lodge packed with Amenities

Top trending hotels in Crumpton

Hampton Inn Middletown

Hampton Inn Middletown

2.5 out of 5
117 Sandhill Dr, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 29 Sept to 30 Sept
AU$206
29 Sept - 30 Sept
includes taxes & fees
With a stay at Hampton Inn Middletown in Middletown, you'll be within a 15-minute walk of Westown and Middletown Historic District.
Opens in a new windowHampton Inn Middletown
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 out of 5
315 Auto Park Dr, Middletown, DE
Fully refundable
The price is AU$197 per night from 29 Sept to 30 Sept
AU$197
29 Sept - 30 Sept
includes taxes & fees
Located in Middletown, Holiday Inn Express & Suites Middletown by IHG is within a 5-minute drive of Dutch Country Farmers Market and Frog Hollow Golf Club.
Opens in a new windowHoliday Inn Express & Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 out of 5
411 MERRIMAC AVENUE, Middletown, DE
Fully refundableReserve now, pay when you stay
The price is AU$177 per night from 19 Oct to 20 Oct
AU$177
19 Oct - 20 Oct
includes taxes & fees
Located in Middletown, Fairfield Inn & Suites by Marriott Middletown is within a 5-minute drive of Westown and Middletown Historic District.
Opens in a new windowFairfield Inn & Suites by Marriott Middletown
Save an average of 15% on thousands of hotels when you're signed in
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 28 Oct to 29 Oct
AU$137
28 Oct - 29 Oct
includes taxes & fees
A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Chestertown Dog Park.
Opens in a new windowRed Roof Inn & Suites Chestertown
Don't see what you're looking for?
See all available properties in Crumpton
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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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^Subject to availability and chosen travel dates.