Book Holiday Homes in Crumpton

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Featured Holiday Homes in Crumpton

Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
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.
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.
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Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Galena
The price is AU$1,791 per night from 17 Apr to 18 Apr
AU$1,791
includes taxes & fees
17 Apr - 18 Apr
When you stay at this vacation home in Galena, you'll be on the waterfront, within a 5-minute drive of Sassafras Harbor Marina and Toal Park.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Lovely Home in Chestertown Which Sleeps 7 -  Free EV Charging for guest

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Chestertown
With a stay at this vacation home in Chestertown, you'll be a 1-minute walk from Kings Town Park and 13 minutes by foot from Historical Society of Kent County ...
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

Worton
When you stay at this vacation home in Worton, you'll be near the beach and within a 5-minute drive of Betterton Community Park.
Newly renovated single family home with attached guest suite
A waterfront gem with dock, kayaks great water views.  Sleeps up to 12.

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront family resort Lodge with private pier, game room and bar

Waterfront family resort Lodge with private pier, game room and 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 family resort Lodge with private pier, game room and bar
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Chestertown
A stay at this vacation home places you in the heart of Chestertown, within a 5-minute drive of Kings Town Park and Historical Society of Kent County ...
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
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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
87 Holiday Homes
Lowest Price
AU$120
Highest Price
AU$1,791
Popular accommodation
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Waterfront w/private pier, pool, Hot Tub, kayaks and in town., Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful., Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest , Newly renovated single family home with attached guest suite, A waterfront gem with dock, kayaks great water views. Sleeps up to 12., Waterfront family resort Lodge with private pier, game room and bar, Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

Top trending hotels in Crumpton

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$184 per night from 5 May to 6 May
AU$184
includes taxes & fees
5 May - 6 May
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
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$185 per night from 20 Apr to 21 Apr
AU$185
includes taxes & fees
20 Apr - 21 Apr
With a stay at Hampton Inn Middletown in Middletown, you'll be within a 15-minute walk of Westown and Middletown Historic District.
Hampton Inn Middletown
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$120 per night from 4 May to 5 May
AU$120
includes taxes & fees
4 May - 5 May
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
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Quality Inn

Quality Inn

2.5 out of 5
190 Stadium St, Gateway North Plaza, Smyrna, DE
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 7 Apr to 8 Apr
AU$158
includes taxes & fees
7 Apr - 8 Apr
With a stay at Quality Inn in Smyrna, you'll be within a 15-minute drive of Dover International Speedway and Bayhealth Emergency Center - Smyrna.
Quality Inn
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.