
Places to stay near Gerry Boyle Park
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Top-rated vacation rentals near Gerry Boyle Park
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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 --

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”.

Sailwinds Waterview Loft at Cambridge Creek
Waterview 2nd 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! All 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! *BOOKING PARTY MUST BE 21 yrs+

Historic Apothecary | 2 Master Suites | Old Town
Majestic, pre-Civil War Italianate brick home in favored southeast Old Town. Steps away from King Street and 2 blocks to the waterfront, location is unbeatable! This 3-story home established in the 1800s served as a former apothecary. New renovations offer utmost luxury, distinctive architecture with genuine hospitality and true sense of history and charm. 2 Masters Suites 4K 65in TVs w/ Streaming Hi-Speed Internet Dedicated Workspace 24 hr Self Check-in Washer/Dryer Free parking upon request

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.

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.

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.

The Loft at Sailor's Retreat. Waterfront Apartment
Romantic waterfront loft for couples in a charming barn. Relax in a cozy king bed, enjoy a full bath, and cook in a well-equipped country kitchen. Sip wine or coffee on your private balcony overlooking the water, or explore the creek with kayaks and paddleboards. Share the pool (Apr–Oct), lawn games, and game room with one other unit. Perfect for a peaceful getaway to unwind and reconnect. Designed as an adults-only retreat—no children please.

Waterfront Oasis! Hot tub! 2+ acres - Sleeps 8
HOT TUB!! WATERFRONT!! Relax with the entire family at this peaceful 3 bedroom fully remodeled private waterfront cottage on a quiet cove off the Choptank River/Chesapeake Bay. Enjoy the incredible views from your bed, from the large screened-in porch, from the oversized deck, from the hammock or double swinging chair out by the water! Launch a kayak right from the property and watch the gorgeous sunrises from the comfort of your bed!

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”).

Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

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 vacation rentals near Gerry Boyle Park
Condo rentals with wifi

Anchors Away

Modern 2 bed 2 bath unit in hip DC neighborhood

1st Floor Condo in Annapolis

Renovated Apt In Historic Dist w/2 Parking Spots

Cozy Old Town Apartment

Annapolis @Gate 1 steps to the Harbor Free parking

Capts Qrtrs - Awesome downtown Annapolis location!

Captains Quarters | Waterfront & Pool
Family-friendly house rentals

Waterfront Getaway with Dock

Osprey's Retreat Waterfront w/ private beach/dock

Newly Renovated Modern 3 bed 2 bath Water Front

Waterfront, Private Pier, Sleeps 10, 4 bedrooms

Soul Oasis - home on the Chesapeake Bay

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Essex Mill Pond

River Refresh - Waterfront with Spa on Placid Bay
Apartment rentals with air conditioning

Nature's Rest in Church Creek

Charming Studio in the heart of St. Michael's, MD.

Blue Crab Lodge

Boutique by the Bay

Beach Highway Hobby Farm

Adorable Waterfront Apt Weekend Getaway & Scones!

Luxury escape in DC now with a private Deck!

Private Annapolis Inlaw Apartment
Other great vacation rentals near Gerry Boyle Park

The Little House on the Farm, Water Access

School Street Retreat: Cozy, artsy, central home

Charming cottage, FP, 1 blk water, historic area

The Cottage at Broad Creek

The Place in Cambridge-Summer is here!

Hambrooks House - Porched Sanctuary near Choptank

Choptank Coastal Cottage

Magical Waterfront Home Dock, Firepit, Family Fun!
Destinations to explore
- FedExField
- Breezy Point Beach & Campground
- Six Flags America
- United States Naval Academy
- Annapolis City Dock
- Downtown Annapolis Partnership
- Quiet Waters Park
- Navy–Marine Corps Memorial Stadium
- Killens Pond State Park
- Westfield
- Salisbury Zoo
- Chesapeake Beach Water Park
- Chesapeake Bay Maritime Museum
- Terrapin Nature Park
- Nassau Valley Vineyards & Winery
- Leonardtown Wharf
- Great Frogs Winery
- Suicide Bridge Restaurant
- Layton's Chance Vineyard and Winery
- General's Ridge Vineyard
- William Preston Lane Junior Memorial Bridge
- Air Mobility Command Museum
- Calvert Marine Museum





