Vacation rentals in Woolford

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Woolford

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

Guest favorite

Farm stay in Madison

4.98 out of 5 average rating, 159 reviews

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Aug 16 – 23

€ 124 per night
Guest favorite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

Close to Blackwater NWR and the Harriet Tubman Center, enjoy peaceful days at our secluded waterfront cottage on Church Creek. Two miles from a main road, and our closest neighbor is across a cove, our estate offers 50 acres of privacy and one of the best waterfront views on the Chesapeake. Enjoy a view from every window and nature all around you. Excellent walking, swimming (in-ground pool-May 3-Oct 1), great birding and bicycling. Launch your kayak from the backyard. Perfect private getaway!

Feb 28 – Mar 7

€ 212 per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 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!

Nov 29 – Dec 6

€ 86 per night

Popular amenities for Woolford vacation rentals

Other great vacation rentals in Woolford

Guest favorite

Guest suite in Cambridge

4.95 out of 5 average rating, 265 reviews

Oakley Suite

Nov 17 – 24

€ 151 per night
Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 203 reviews

Peaceful Waterfront Retreat on The Bay

Oct 22 – 29

€ 154 per night
Guest favorite

Guesthouse in Cambridge

4.99 out of 5 average rating, 109 reviews

Rosses Chance Guest House

Jul 9 – 16

€ 239 per night
Guest favorite

Home in Lusby

4.98 out of 5 average rating, 259 reviews

Cove Point Beach Cabin

Dec 22 – 29

€ 179 per night
Guest favorite

Guesthouse in Lusby

4.97 out of 5 average rating, 131 reviews

Cozy Lakeside Studio Retreat.

May 5 – 12

€ 135 per night
Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Feb 25 – Mar 4

€ 138 per night
Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 112 reviews

Black Walnut Cove Retreat, Tilghman Island

Apr 5 – 12

€ 151 per night
Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

Sep 3 – 10

€ 161 per night
Guest favorite

Home in Lusby

5.0 out of 5 average rating, 110 reviews

Historic Rousby Hall, Waterfront, Patuxent River

Oct 20 – 27

€ 758 per night
Guest favorite

Home in Cambridge

4.97 out of 5 average rating, 88 reviews

Church Creek Charm (close to Blackwater Refuge)

Jul 25 – Aug 1

€ 154 per night
Guest favorite

Guesthouse in Cambridge

5.0 out of 5 average rating, 12 reviews

Camelot Cottage

Jun 10 – 17

€ 96 per night
Guest favorite

Cottage in Woolford

5.0 out of 5 average rating, 38 reviews

Fishing Cottage near Cambridge & Blackwater Refuge

Oct 22 – 29

€ 313 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Dorchester County
  5. Woolford