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Vacation rentals in Woolford

Vacation rentals in Woolford

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Woolford

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

Newly Renovated Modern 3 bed 2 bath Water Front
SUPERHOSTEntire house · 6 guests · 3 beds · 2 bathrooms
Newly Renovated Modern 3 bed 2 bath Water Front

Newly renovated waterfront home with all the amenities needed to enjoy your Eastern Shore getaway. Less than 10 minutes from Downtown Cambridge and the Chesapeake Bay Hyatt.

What guests are saying:

“What a lovely spot! Our family (2 adults and 2 preschoolers) desperately needed a change of scenery, but wanted somewhere we could continue to socially distance. We picked this house for the private river access and yard space, in driving distance to DC. The house was beautifully appointed and updated, with a totally stocked kitchen and garage full of outdoor gear. All beds and furniture were comfortable! Our youngest used the provided pack n play and high chair, which were so handy. They also had games, books and toys for kids - the Disney DVD bingo game was a surprise highlight! We enjoyed the kayaks and canoe with easy launch points. We had hoped to wade or swim in the water, but the vegetation in the river wasn't super inviting. (There wasn't any false advertising here, just my own misguided hope.) You may need to bring your own firewood if you plan to make s'mores in the firepit - we could only find Duralogs which we didn't think were taste safe. Since we were trying to maintain distance, we didn't explore the area as much as we would have liked. We had delicious take-out from Bombay Tadka in Cambridge, and had a blast at Emily's Produce for u-pick strawberries. We enjoyed the stars at night from the patio as well!”

Chesapeake Sunset Cottage
SUPERHOSTEntire cottage · 4 guests · 2 beds · 2 bathrooms
Chesapeake Sunset Cottage

Only sunsets and stars. No neighbor. Surrounded on three sides by water. Totally quiet. Modern but peaceful. On flight path of migratory geese, swans, ducks, osprey. Bald eagles are plentiful. Perfect for couples who want to recharge their lives.

What guests are saying:

“I loved my stay at the Chesapeake Sunset Cottage. The living room was very comfortable. The projector was excellent. The view of the water was also excellent. When we went crabbing, we caught 1 but when we checked again it was gone then we realized why we only caught 1 the door was open. Overnight we got 2 but we had to leave the following day so we let them go. We went kayaking off the floating dock it was very easy to get it into the water. The screened in porch was nice for breakfast and hearing the morning bird chorus. We loved the pool and all the rafts provided. The down town was very cute and I will recommend the Sunnyside Gift Shop, the Blue Awning, and the Black Water Café. I absolutely loved my stay at the Chesapeake Sunset Cottage and I cannot wait to go again. -Tessa”

Church Creek  Natures' Rest
SUPERHOSTEntire flat · 4 guests · 1 bed · 1 bathroom
Church Creek Natures' Rest

Nature's Rest is ideally located, just minutes to Blackwater Wildlife Refuge The Harriet Tubman Museum, as well as boat ramps for easy access to the Chesapeake Bay and it's tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

What guests are saying:

“Wende’s place is a little gem , and a real bargain to boot. My family and I were able to act responsibly and still have a blast in this cute little corner of the Chesapeake Bay. The layout of this Airbnb is roomy and allows for some privacy for a family of four. There is a lovely little deck where you can enjoy the evening air and watch the hummingbirds dance around the feeder. You will need some bug spray or citronella candles, but that won’t keep you from enjoying the moon rise in this outdoor space. Wende’s place is located in a very rural area, but still close to everything you might need. Wende gave us some great tips regarding where to get wonderful steamed crabs, and also steered us towards a lovely outdoor dining place in Saint Michaels on the water. Unfortunately, the Harriet Tubman visitor center was still close, but the Black Water wildlife refuge was stunningly beautiful . We even had our own private fireworks display on the Fourth of July. We watched as a 15 minute display blossomed over the volunteer fire department building at the end of the block. All in all , it was a perfectly lovely long weekend in beautiful Dorchester County. I would definitely stay here again.”

Holiday rentals for every style

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Popular amenities for Woolford holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Woolford

Church Creek Getaway
SUPERHOSTEntire house
Church Creek Getaway
Price:£107 / night
Madison Nature Getaway
SUPERHOSTPrivate room
Madison Nature Getaway
Price:£73 / night
Madison Bay Water View Getaway Corner
Private room
Madison Bay Water View Getaway Corner
Price:£50 / night
Dorothy's Chesapeake Delight
SUPERHOSTEntire house
Dorothy's Chesapeake Delight
Price:£123 / night
Little Farmhouse by the Bay
Entire house
Little Farmhouse by the Bay
Price:£192 / night
Oakley Suite
SUPERHOSTEntire guest suite
Oakley Suite
Price:£89 / night
Harwood Cottage on Church Creek, water access
Entire cottage
Harwood Cottage on Church Creek, water access
Price:£156 / night
IRONMAN - EagleMan - Cambridge - Nautical  - Queen
SUPERHOSTPrivate room
IRONMAN - EagleMan - Cambridge - Nautical - Queen
Price:£188 / night
Guest House on Eagle/Ironman Bike Course.
Entire house
Guest House on Eagle/Ironman Bike Course.
Price:£100 / night
Eagleman and Ironman Oasis
Entire house
Eagleman and Ironman Oasis
Price:£575 / night
Sunset Breezes - a quiet retreat
Entire flat
Sunset Breezes - a quiet retreat
Price:£153 / night
Sailor's Retreat Pineapple Room
Private room
Sailor's Retreat Pineapple Room
Price:£96 / night
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