
Places to stay near Gerry Boyle Park
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Top-rated holiday rentals near Gerry Boyle Park
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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.

Little Slice of Cambridge. 2 bedroom, pet friendly
You’ll be staying right in the center of the Historic district, close enough to walk to town and enjoy shopping or some of the great restaurants. Just two blocks from the water, a short stroll to the lighthouse or down to the water front and enjoy the park. This newly listed 2 bedroom , pet- friendly apartment has everything you will need to explore the history, food and waterfowl found in this area. Park your boat here. We can’t wait for you to experience Cambridge and relax in the “West End”.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

The Little House on the Farm, Water Access
Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

Peaceful Historic House Near Water, with Hot Tub!
Peaceful 3 bedroom/1.5 bath Victorian house near the water. Located in Historic West End, this 1900 house has been recently renovated to accentuate its historic charm while delivering all the modern comforts. Just a short walk from Long Wharf Park, the Choptank River Lighthouse, and downtown Cambridge with great restaurants and shops. Amenities include air conditioning/heating, a hot tub, WIFI, a back deck and grill, front porch with rocking chairs, and a fire pit with Adirondack chairs.

Sailwinds Waterview Loft at Cambridge Creek
Waterview Second Story loft apartment in downtown Cambridge, MD with private entrance and secure bike storage! Located just 4 blocks from Route 50 and only 2 blocks from the Choptank River! This amazing space is within walking distance to seafood restaurants, shops, public boat ramp, beach, and parks! Close to all local attractions including the Choptank River Lighthouse, Sailwinds Park, Harriett Tubman UnderGround Railroad, Blackwater Refuge, Eagleman/Iron Man, and so many more!

Sunset Breezes - quiet waterfront retreat
Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

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.

Waterfront-View of Bay from your Bed
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Waterfront, Private Pier, Sleeps 10, 4 bedrooms
Escape to our waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure for everyone. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Water's Edge Cottage | Luxury Retreat
We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

High St. Art Gallery Suite
This boutique suite is adjoined to the future home of High St. Art Gallery. This historic home was built in 1796 and is being lovingly restored by three generations of a family committed to creating beautiful, unique and comfortable spaces that can be a retreat away from home. This suite has all the details and delights that will make your stay enjoyable and we hope you will come again and again.
Popular amenities for holiday rentals near Gerry Boyle Park
Apartment rentals with wifi

Oceanfront 2 Bed/1.5 Bath, Balcony, Pools, Lounge

Renovated Apt In Historic Dist w/2 Parking Spots

Capts Qrtrs - Awesome downtown Annapolis location!

Annapolis @Gate 1 steps to the Harbor Free parking

Gorgeous Beachfront! King Bed, Direct Ocean View!

1st Floor Condo in Annapolis

Coastal 2BR • 10 min to Beach & Trails

Beachfront with a View and Amenities Galore
Family-friendly house rentals

Church Creek Charm (Close to Blackwater!)

Soul Oasis - home on the Chesapeake Bay

Waterfront Getaway with Dock

Waterfront with sweeping bay view & private beach

Newly Renovated Modern 3 bed 2 bath Water Front

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Kent Island Waterfront Home with Amazing Sunsets

The Little Gypsy BoHome
Apartment rentals with air conditioning

Stunning 1BR Apt. in Historic Row Home w/ Parking

Blue Crab Lodge

Secluded and romantic getaway in Chestertown

Morning Light Apartment

Butchershill- Clean, Fireplace, King Bed, Parking!

Luxury escape in DC now with a private Deck!

Cozy Waterfront Apartment Chester, MD

Charming Studio in the heart of St. Michael's, MD.
Other great holiday rentals near Gerry Boyle Park

The Place in Cambridge-Spring is in the Air!

Tranquility on Talbot

Cozy Guest House Near Park

Hambrooks House - Porched Sanctuary near Choptank

Charming Cambridge Cottage | Walk to River + Town

Charming cottage, FP, 1 blk water, historic area

High Water Guest House

Talbot Corner: Dog-Friendly 3-Bedroom Home
Destinations to explore
- Sandy Point State Park
- Six Flags America
- Breezy Point Beach & Campground
- Quiet Waters Park
- Annapolis City Dock
- Killens Pond State Park
- Navy–Marine Corps Memorial Stadium
- Salisbury Zoo
- Calvert Marine Museum
- FedExField
- Westfield
- Chesapeake Beach Water Park
- Downtown Annapolis Partnership
- Nassau Valley Vineyards & Winery
- Chesapeake Bay Maritime Museum
- Point Lookout State Park
- Layton's Chance Vineyard and Winery
- General's Ridge Vineyard
- Terrapin Nature Park
- Suicide Bridge Restaurant
- Leonardtown Wharf
- Air Mobility Command Museum





