
Places to stay near Gerry Boyle Park
Book unique holiday rentals, homes and more on Airbnb
Top-rated holiday rentals near Gerry Boyle Park
Guests agree: these stays are highly rated for location, cleanliness and more.

Relaxing Water Views - Mill Creek Cottage
Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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”.

Beach Front and 'Perfectly Placed'
Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

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.

Blue Crab Lodge
Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

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.

Great Historic Cambridge Home With Parking!
This is a beautifully renovated home three blocks from the Choptank River. It's three finished levels and will easily accommodate a large group. This is a short walking distance to downtown Cambridge. I use this as a weekend getaway and make it available when I know I will not be there. It has been lovingly renovated and decorated with that in mind.
Popular amenities for holiday rentals near Gerry Boyle Park
Apartment rentals with wifi

Renovated Apt In Historic Dist w/2 Parking Spots

Capts Qrtrs - Awesome downtown Annapolis location!

Annapolis @Gate 1 steps to the Harbor Free parking

Anchors Away

Captains Quarters | Waterfront & Pool

Newly Renovated 1BR Condo Sleeps 2 - Unit 1

1st Floor Condo in Annapolis

Cozy Old Town Apartment
Family-friendly house rentals

Waterfront Getaway with Dock

Peace Point - Waterfront, Secluded, Home w/hot tub

Hambrooks House - Porched Sanctuary near Choptank

Beautiful Renovated Cottage at Iron Man Start Line

3BR Luxury Retreat, Pond, Gym, Near DC

Talbot Corner: Dog-Friendly 3-Bedroom Home

Hidden Gem In Heart of Cambridge with Pool!

Historic Rousby Hall, Waterfront, Pool, Beach
Apartment rentals with air conditioning

Our Little Piece of Heaven

Serenity Suite on Chesapeake Bay

Morning Light Apartment

Beach Highway Hobby Farm

Luxury escape in DC now with a private Deck!

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

Spacious Beach House Top Floors - Walk Everywhere!

Nature's Rest in Church Creek
Other great holiday rentals near Gerry Boyle Park

The Place in Cambridge-Summer is here!

The Drinking Gourd: Stunning Cambridge Penthouse

Charming Cambridge Cottage | Walk to River + Town

Magical Waterfront Home Dock, Firepit, Family Fun!

Charming cottage, FP, 1 blk water, historic area

Hideaway on the Bay: Waterfront Vintage A Frame

Rosses Chance Guest House

The Little House on the Farm, Water Access
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
- Calvert Marine Museum
- Westfield
- Salisbury Zoo
- Chesapeake Beach Water Park
- Nassau Valley Vineyards & Winery
- Chesapeake Bay Maritime Museum
- Terrapin Nature Park
- Leonardtown Wharf
- Great Frogs Winery
- Air Mobility Command Museum
- Suicide Bridge Restaurant
- General's Ridge Vineyard
- Layton's Chance Vineyard and Winery
- William Preston Lane Junior Memorial Bridge





