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Vacation rentals in Jumptown

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Top-rated vacation rentals in Jumptown

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Tiny home in Cambridge

4.89 out of 5 average rating, 500 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Aug 21 – 28

ﺩ.ﺇ309 per night

Houseboat in Grasonville

4.99 out of 5 average rating, 117 reviews

Cass-Away A Luxury Houseboat

Kent Narrows Rentals welcomes you aboard Cass-Away! A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a living room, kitchen, 2 bedrooms, 2 full baths, and a magnificent view from the rooftop deck! With 9 waterfront bars/restaurants within walking distance, you can get a taste of what the eastern shore has to offer. Minutes from the Bay Bridge and a short drive to Annapolis, D.C., St. Michael’s, and Ocean City. NO Fishing/Crabbing on property! Check our website for more info!

Feb 10 – 17

ﺩ.ﺇ640 per night

Guest suite in Arnold

4.96 out of 5 average rating, 569 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Jul 18 – 25

ﺩ.ﺇ411 per night

Apartment in Greenwood

4.97 out of 5 average rating, 482 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Jan 20 – 27

ﺩ.ﺇ302 per night

Casa particular in Chestertown

4.93 out of 5 average rating, 103 reviews

Red, White & Waterview Studio Apt with pool

One bedroom, one full bath, studio apartment. Private off the street parking and entrance. We invite you to enjoy everything our private residence has to offer: private inground pool, seasonal hot tub, lush grounds and outdoor seating. The space is well equipped w/ a queen sized bed, linens, washer/dryer, microwave, fridge, dinette, full size sofa bed, toiletries... everything you could possibly need to escape the hustle and bustle of life. Flat walk to the historic Chestertown waterfront!

Mar 28 – Apr 4

ﺩ.ﺇ499 per night

Apartment in Magnolia

4.95 out of 5 average rating, 120 reviews

Perfect Rental for Dover Attractions & BayBeaches

15 minutes from Dover Nearby casinos, beaches, and the racetrack. Bowers and Slaughter beaches are about 10-15 mins from us, whereas, the major beaches like Rehoboth, Lewes and Dewey are 45mins to an hour from us. We are 5 mins from Highway 1 and located 15 mins from DE Sports Complex 10 mins from Highway 13 (Dupont Ave) Near the mall, casino, racetrack, shopping, and many restaurants. Killens Pond State Park is a 10 min drive. Harrington Casino the Del. State Fair is 15 mins from us.

Dec 15 – 22

ﺩ.ﺇ420 per night

Loft in Lusby

5.0 out of 5 average rating, 316 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Jan 20 – 27

ﺩ.ﺇ506 per night

Apartment in Frederica

4.97 out of 5 average rating, 260 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

Mar 31 – Apr 7

ﺩ.ﺇ324 per night

Guest suite in Chestertown

4.99 out of 5 average rating, 193 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Jul 9 – 16

ﺩ.ﺇ486 per night

Guesthouse in Easton

4.99 out of 5 average rating, 547 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Aug 24 – 29

ﺩ.ﺇ590 per night

Cottage in Saint Michaels

4.99 out of 5 average rating, 138 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

Oct 25 – Nov 1

ﺩ.ﺇ1,966 per night

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Dec 14 – 21

ﺩ.ﺇ447 per night

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Popular amenities for Jumptown vacation rentals

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Air conditioning

Other great vacation rentals in Jumptown

Guesthouse in Annapolis

4.9 out of 5 average rating, 209 reviews

Calico Cottage Guest House, king bed, free parking

Dec 15 – 22

ﺩ.ﺇ360 per night

Apartment in Pasadena

4.99 out of 5 average rating, 550 reviews

Sea Dreamer aka Phenomenal Hospitality

Oct 30 – Nov 6

ﺩ.ﺇ346 per night

Home in Annapolis

4.96 out of 5 average rating, 112 reviews

Historic Downtown in-law suite

Mar 23 – 30

ﺩ.ﺇ446 per night

Guesthouse in Annapolis

4.97 out of 5 average rating, 197 reviews

RECENTLY RENOVATED Cottage Near Downtown Annapolis

Sep 20 – 27

ﺩ.ﺇ460 per night

Home in Cambridge

4.92 out of 5 average rating, 182 reviews

Guest House: Farm homestead

Oct 9 – 16

ﺩ.ﺇ458 per night

Home in Greensboro

4.96 out of 5 average rating, 49 reviews

Cozy 2 bedroom home on wooded private lane

Jan 23 – 30

ﺩ.ﺇ471 per night

Bungalow in Queen Anne

4.94 out of 5 average rating, 53 reviews

Private bungalow with fire pit near Easton, Denton

Nov 30 – Dec 7

ﺩ.ﺇ829 per night

Guesthouse in Wye Mills

4.94 out of 5 average rating, 17 reviews

Adorable Lake Front 1BR Cottage-fully furnished!

Sep 26 – Oct 3

ﺩ.ﺇ319 per night

Destinations to explore