
Places to stay near Layton's Chance Vineyard and Winery
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Top-rated vacation rentals near Layton's Chance Vineyard and Winery
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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 --

River House on the Choptank
Welcome to the River House! Stay in our renovated home on the Choptank River of MD's Eastern Shore, with your own low-tide beach and magnificent sunsets. We offer a peaceful location and thoughtful detail, creating a memorable getaway for a relaxing weekend or remote work location. Enjoy a day on the river with our paddle board or 2 kayaks, and end the day around the firepit. In cool weather, cozy up next to the fireplace. Also, visit nearby towns--St. Michaels, Easton, Oxford, and Chestertown.

Private Waterfront Home W/ Hot Tub, Dock & Kayaks
Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

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!

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.

Blackwater & Snakehead Farm "She Shed" Tiny House
The "She Shed" Tiny House is the best bargain & unique stay around! This Tiny House is made from a traditional 10'x18' shed and is solar powered! It's surprisingly spacious with a full size bathroom, kitchenette, lofted twin bed, day bed & trundle bed! The home borders a sheep pasture, barn, goat pasture & chicken coop! Snakehead fishing is just a short walk away! Kayacks & creek launch on site! Just a 5 minute drive from Blackwater Refuge! Relax and enjoy country living!

Waterfront Getaway with Dock
Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

4bed/4.5bath Lux Farmhouse/Pool/Gym/5 min from SU
BEFORE BOOKING: Pool will be open 4/05/26 Unless PRIOR AUTHORIZATION….. NO PARTIES/NO EVENTS/NO GATHERINGS, only the amount of guests in your party are allowed on the property. Fully restored top to bottom 1920s farm house. Every bedroom has its own full bathroom Full laundry room with extra refrigerator RH furniture All bedding/towels/paper towels/toilet paper/body wash/shampoo/conditioner/spices/laundry detergent included;Total turn key

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!

One of a kind waterfront home with private dock
Beautiful 2 bedroom/1 bathroom waterfront getaway, with full kitchen and bath, loaded with amenities from coffee, cookware, charcoal grill to crabbing, fishing and kayaks. At the end of the day, gather around the backyard or take a walk down the 125+ foot pier for scenic views as the sun sets on the Wicomico River. Less than a 10 minute drive to the Red Roost and Bull Lips Dock Bar or head to Green Hill Country Club for a round of golf.

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”).

Coastal Waterfront 1 Bedroom Cottage
This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.
Popular amenities for vacation rentals near Layton's Chance Vineyard and Winery
Condo rentals with wifi

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

Elegant Condo with a Spacious Porch

Breezy Point #305 - Rooftop Deck Panoramic Sunsets

Beach Sunrise: Walk to Downtown & Lewes Beach

Gorgeous Beachfront! King Bed, Direct Ocean View!

Barnyard Retreat

Stylish Coastal Loft Minutes to Rehoboth & Lewes

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Family-friendly house rentals

Soul Oasis - home on the Chesapeake Bay

High St. Art Gallery Suite

Waterfront with sweeping bay view & private beach

The Little House on Back Creek

Beach Please! River cottage w/private beach & dock

Kent Island Waterfront Home with Amazing Sunsets

The Little Gypsy BoHome

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

Our Little Piece of Heaven

Blue Crab Lodge

Historic St. Mary's City, MD

Little Slice of Cambridge. 2 bedroom, pet friendly

Beach Highway Hobby Farm

Cozy Waterfront Apartment Chester, MD

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

Spacious Beach House Top Floors - Walk Everywhere!
Other great vacation rentals near Layton's Chance Vineyard and Winery

Relaxing Water Views - Mill Creek Cottage

Beautiful Waterfront Getaway on the Choptank River

Cove Point Lighthouse Keeper's House- Side B

“Cabana by the Bay”-tiny home on a pier!

Cottage on Cabin Creek

The River House

Rosses Chance Guest House

The Cottage at Broad Creek
Destinations to explore
- Ocean City Beach
- Ocean City Boardwalk
- Ocean City Boardwalk
- Chincoteague Island
- Broadkill Beach
- Assateague Island National Seashore
- Sandy Point State Park
- Rehoboth Beach
- Northside Park
- Assateague State Park
- Jolly Roger Amusement Park
- Delaware Seashore State Park
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Fenwick Island State Park Beach
- Breezy Point Beach & Campground
- Ocean Pines Golf Club
- Dewey Beach Access
- Annapolis City Dock
- Quiet Waters Park
- United States Naval Academy
- Roland E Powell Convention Center
- Gerry Boyle Park
- Killens Pond State Park





