Crumpton Vacation Rentals

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Check prices for these dates

Tonight
Jun 19 - Jun 20
Tomorrow
Jun 20 - Jun 21
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Crumpton

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Dining

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (35)
"Was a great vacation hope to come back next year!"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Outdoor dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

10.0 out of 10, Exceptional, (45)
"Cool house within walking distance to beach, restaurant and marinas"
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
Fridge, microwave, oven, stovetop

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

9.8 out of 10, Exceptional, (87)
"In the area for a wedding. This was a great place for the family to gather in between events. Communication with the owners is top notch. We highly recommend it. "
Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10.0 out of 10, Exceptional, (40)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Marina

Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.

10.0 out of 10, Exceptional, (7)
"Property was extremely well kempt. It was beautiful. We enjoyed ourselves there and would recommend it to others."
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (20)
"Everything about the place was great! Easy check in and super clean and homey feeling spot. Would recommend to anyone looking for a quiet and comfy place on the eastern shore. We will definitely be booking again if we come back to the area!"
The price is ￥32,625
￥53,357 total
includes taxes & fees
Jun 22 - Jun 23
Waterfront Retreat with Private Dock and Beach
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (9)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Property grounds

Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!

10.0 out of 10, Exceptional, (21)
"Good location."
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (2)
"Amazing place to stay. Plenty of space, the owners go above and beyond for on amenities. The house was very clean."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (14)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
1 bedroom, bed sheets

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (6)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (110)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (37)
"A must book!"
Serene Waterfront Cottage with dock and gorgeous views.
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (4)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is ￥28,580
￥65,032 total
includes taxes & fees
Jun 23 - Jun 24
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Property grounds

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

10.0 out of 10, Exceptional, (15)
"Extremely clean, comfortable, and cozy place to stay for a weekend trip. The host was great to work with. We would definitely stay again."
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
BAYSIDE BUNGALOW
Sauna

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (39)
"Beautiful, cozy cottage. So peaceful and pretty. Owners are on site and are great people. We have stayed here several times and look forward to coming back soon."
The price is ￥29,000
￥43,651 total
includes taxes & fees
Jun 23 - Jun 24
BAYSIDE BUNGALOW
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

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
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (33)
"We love this place and would stay here again in a heartbeat. Beautifully decorated with so many details and touches that make it extra special. Such a well done lovely property!!!"
Historic Downtown Garden Oasis with Private Patio
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (13)
"Fantastic accommodations! Many amenities! Friendly hostess! "
The price is ￥8,874
￥17,091 total
includes taxes & fees
Jun 26 - Jun 27
Guest Suite for up to 2 in a Victorian on the Chester River
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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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 air-conditioning 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 Tilmon's Island Winery and Church Hill Theatre.

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.