Vacation rentals in Crumpton

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Crumpton

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Farm stay in Chestertown

4.94 out of 5 average rating, 106 reviews

Outrange at Blue Heron Farm

Enjoy the peace and tranquillity at “Outrange,” Blue Heron Farm’s recently updated cabin. This unique and rustic 2 bedroom, 1 bath home was designed by architect Randy Wagner and built in 1978. Tucked away on a 126 acre fourth-generation organic waterfront farm, Outrange is a private getaway situated just 15 minutes from historic Chestertown. With views of the Chester River and access to the farm’s private dock, Outrange is a magical getaway for anyone that loves the beauty of the Eastern Shore.

Feb 2 – 9

€ 241 per night
Guest favorite

Apartment in Chestertown

4.97 out of 5 average rating, 188 reviews

Quiet escape in center of town

Escape to a secluded, romantic studio hideaway in the middle of Chestertown. Private parking, and over 1 acre of gardens to call your own. Relax in front of the fire with views of gardens in every window. Kitchenette has extra large toaster oven, (can cook pizza and roast chicken), 2 burner hot plate, microwave, refrigerator, and Keurig/coffee makers. Comfortable king bed with luxury linens, kitchenette, and washer dryer. We also host ‘Wren Retweet”, a house in front of the carriage house.

Aug 2 – 9

€ 197 per night
Guest favorite

Cabin in Chestertown

4.98 out of 5 average rating, 215 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Sep 28 – Oct 5

€ 318 per night

Popular amenities for Crumpton vacation rentals

Other great vacation rentals in Crumpton

Guest favorite

Home in Millington

4.91 out of 5 average rating, 32 reviews

The Peaceful Getaway (with private pool & hot tub)

May 19 – 26

€ 396 per night
Guest favorite

Apartment in Chestertown

5.0 out of 5 average rating, 64 reviews

Waterfront historic district 1BR Apartment

Jun 6 – 13

€ 161 per night
Guest favorite

Home in Millington

4.91 out of 5 average rating, 11 reviews

Lark's Nest on the Chester River

Sep 2 – 9

€ 231 per night
Guest favorite

Casa particular in Chestertown

4.93 out of 5 average rating, 99 reviews

Red, White & Waterview Studio Apt with pool

Nov 27 – Dec 4

€ 137 per night
Guest favorite

Apartment in Dover

4.88 out of 5 average rating, 84 reviews

Cozy apartment in a quiet Amish country setting

May 19 – 26

€ 105 per night
Guest favorite

Home in Chestertown

5.0 out of 5 average rating, 75 reviews

River front cottage with private dock & water fun

Apr 5 – 12

€ 526 per night
Guest favorite

Apartment in Chestertown

4.92 out of 5 average rating, 95 reviews

Downtown Studio Apartment

Jan 4 – 11

€ 139 per night
Guest favorite

Home in Galena

4.89 out of 5 average rating, 70 reviews

Yellow Door Cottage

Jun 23 – 30

€ 200 per night
Guest favorite

Home in Greensboro

4.95 out of 5 average rating, 44 reviews

Cozy 2 bedroom home on wooded private lane

Oct 4 – 11

€ 126 per night
Guest favorite

Apartment in Clayton

4.95 out of 5 average rating, 40 reviews

Quaint 1 BR apt in Historic Firehouse

Sep 7 – 14

€ 104 per night
Guest favorite

Apartment in Kent County

4.92 out of 5 average rating, 73 reviews

Furnished country apartment!

Aug 29 – Sep 5

€ 104 per night
Guest favorite

Cottage in Charlestown

4.98 out of 5 average rating, 43 reviews

Long Beach Cottage, (romantic couple’s getaway)

Nov 28 – Dec 5

€ 441 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Queen Anne's County
  5. Crumpton