Places to stay near Gerry Boyle Park

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Top-rated vacation rentals near Gerry Boyle Park

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Guest favorite

A breathtaking sunrise is captured over calm waters, creating a stunning reflection of vibrant hues of orange, pink, and purple. The private pier is visible on the right, complementing the serene landscape of trees on the distant shore and a tranquil island in the background.

Cottage in Edgewater

4.99 out of 5 average rating, 155 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Top guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 148 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Superhost

The house is positioned among leafy trees, featuring numerous large windows that brighten the interior. A spacious deck is visible, along with a hot tub. A stone fire pit surrounded by wooden chairs is located in the foreground, inviting outdoor gatherings.

Home in Montross

4.88 out of 5 average rating, 232 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million+ old shark teeth, and a fossil cliff beach. Fishing! Hot tub on the patio! Bald eagle sightings! Theater Room!

Guest favorite

Home in Frederica

4.92 out of 5 average rating, 324 reviews

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

Top guest favorite

Cottage in Frankford

4.99 out of 5 average rating, 152 reviews

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Top guest favorite

A serene backyard scene is captured at sunset, featuring a concrete patio with four chairs arranged around a small table. A shed is visible in the distance, alongside lush green grass and mature trees. The sky displays a gradient of colors as daylight fades.

Home in Fruitland

4.97 out of 5 average rating, 130 reviews

Amazingly convenient yet secluded.

Our place has views; the yard has beautiful shade trees that set the mood for deep relaxation. One can walk to Walmart, Denny's, Hampton Inn Suites, Ruby Tuesdays and many other business's in minutes. Ocean City is about a 35minute drive. Salisbury University is a five minute drive. UMES is a 13 minute drive.This home is ideally located. A retired teacher on one side is your closest neighbor; on the other property is a caregiver. Needless to say this is a very safe place; enjoy.

Guest favorite

A wooden dock extends over calm waters, featuring four Adirondack chairs arranged facing the serene view. A light casts a soft glow on the water's edge, and the distant shoreline is lined with trees and structures, hinting at nearby activity.

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Superhost

A welcoming living area features a stone fireplace and a large television displaying a serene landscape. A wooden dining table is accompanied by black chairs, and natural light is complemented by a stylish chandelier. Comfortable gray seating invites relaxation in this cozy space.

Home in Georgetown

4.82 out of 5 average rating, 160 reviews

Maplewood - Simply Comfortable, Dog Friendly

Have fun with the whole family at this stylish place in the center of it all. Near the beach, away from the crowds. Local attractions: Sandhill Fields - .5 miles Sports at the Beach - 1 mile Dogfish Head Brewery - 5 miles Lewes Beach -8 Cape May Lewes Ferry Terminal Cape Henlopen State Park Tanger Outlets - 12.4 miles - 13.9 miles And lots of other tax free shopping. Rehoboth Beach Boardwalk - 17.5 miles Dover Downs - 39.1 miles Many other attractions nearby.

Top guest favorite

Two Adirondack chairs are positioned beside a wooden dock, shaded by a large umbrella. The view overlooks calm water surrounded by greenery, creating a serene environment. A small table is present between the chairs, enhancing the inviting outdoor seating area.

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favorite

Home in Cambridge

4.98 out of 5 average rating, 127 reviews

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene 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. 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!

Superhost

A wooden deck leads down to a gravel path surrounded by lush greenery. Two red chairs are positioned on the gravel area, enjoying the serene view of the woods. Soft landscape lighting is present along the path, enhancing the natural surroundings.

Tiny home in Salisbury

4.83 out of 5 average rating, 127 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Guest favorite

A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.

Cottage in Saint Leonard

4.96 out of 5 average rating, 136 reviews

Block to Beach, Screened deck, Hot Tub, No CF

Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) (No cleaning fee and multi night discounts! Message us for monthly rates.)