Book Holiday Homes in Crumpton

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Featured Holiday Homes in Crumpton

Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
With a stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Kings Town Park and Historical Society of Kent County Maryland.
Pet-Friendly Home on Chester River w/ Dock!
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
The price is AU$467 per night from 25 Aug to 26 Aug
AU$467
25 Aug - 26 Aug
includes taxes & fees
Located in Rock Hall, this vacation home is within a 15-minute walk of Ferry Park and Waterman’s Museum.
BAYSIDE BUNGALOW
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Rock Hall
With a stay at this vacation home in Rock Hall, you'll be within a 15-minute drive of The Mainstay and Waterman’s Museum.
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets
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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.
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 15-minute walk of Waterman’s Museum and Rock Hall Harbor.
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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.
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Waterfront Estate w Private Pier, Game Room & Bar

Waterfront Estate w Private Pier, Game Room & Bar

Centreville
Located in Centreville, this vacation home is on a river, within a 10-minute drive of Hazel Miner Monument and Earle Landing.
Waterfront Estate w Private Pier, Game Room & Bar
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.
Entire Townhouse in Rock Hall
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Betterton
With a stay at this vacation home in Betterton, you'll be on the waterfront, just a 4-minute walk from Betterton Historic District and 7 minutes by foot from ...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
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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$123
Highest Price
AU$467
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, BAYSIDE BUNGALOW, Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Waterfront w/private pier, pool, Hot Tub, kayaks and in town., Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Waterfront Estate w Private Pier, Game Room & Bar, Entire Townhouse in Rock Hall, Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

Top trending hotels in Crumpton

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 17 Aug to 18 Aug
AU$190
17 Aug - 18 Aug
includes taxes & fees
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical ...
Comfort Inn & Suites Chestertown
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$123 per night from 18 Aug to 19 Aug
AU$123
18 Aug - 19 Aug
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.
Red Roof Inn & Suites Chestertown
Holiday Inn Express And Suites Middletown by IHG

Holiday Inn Express And 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 24 Aug to 25 Aug
AU$197
24 Aug - 25 Aug
includes taxes & fees
Located in Middletown, Holiday Inn Express And Suites Middletown by IHG is within a 5-minute drive of Dutch Country Farmers Market and Frog Hollow Golf ...
Holiday Inn Express And Suites Middletown by IHG
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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$182 per night from 3 Sept to 4 Sept
AU$182
3 Sept - 4 Sept
includes taxes & fees
Located in Middletown, Fairfield Inn & Suites by Marriott Middletown is within a 5-minute drive of Westown and Middletown Historic District.
Fairfield Inn & Suites by Marriott Middletown
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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.