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Places to stay near Layton's Chance Vineyard and Winery

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Top-rated holiday rentals near Layton's Chance Vineyard and Winery

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Guest favourite
A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.
Home in Preston

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.

FamilyValueWi-Fi

4.92 out of 5 average rating, 129 reviews
Top Guest favourite
The little house is nestled in a serene rural setting, surrounded by greenery and farmland. A gravel pathway leads up to the front door, flanked by simple flower pots. The landscape features open fields in the background, enhancing the peaceful ambience.
Tiny home in Cambridge

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!

ValueFamilyKitchen

4.98 out of 5 average rating, 249 reviews
Guest favourite
An attic bedroom features two spacious beds, each adorned with warm-toned pillows and throws. Bright overhead lights accentuate the light-colored walls and wooden floor, while a decorative area rug adds texture. A window provides natural light, enhancing the peaceful atmosphere.
Home in Salisbury

1900's Modern Farmhouse on 7.5 private acres

Welcome to our 1900's farmhouse. This home has been lovingly updated and maintained over the past century, and sits on 7.5 acres. While it is private and peaceful, its location is minutes away from everything making it easy to get around. Enjoy spacious living and endless outdoor fun in our dedicated game barn (ping pong, cornhole!) and large pastures (frisbee golf, soccer!). This family-friendly home blends historic charm with modern comforts, perfect for creating unforgettable memories.

FamilyLocationCleanliness

4.93 out of 5 average rating, 141 reviews
Guest favourite
A spacious backyard features a circular fire pit surrounded by Adirondack chairs. A picnic table sits to one side, and a hot tub is partially shielded by evergreen trees and a wooden fence, providing a serene outdoor retreat.
Home in Cambridge

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.

ValueFamilyHeating

4.94 out of 5 average rating, 190 reviews
Top Guest favourite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

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.

FamilyValueOutdoor spaces

4.99 out of 5 average rating, 230 reviews
Top Guest favourite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford

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!

LocationFamilySleep quality

4.93 out of 5 average rating, 198 reviews
Top Guest favourite
A scenic view of a spacious green lawn bordering a tranquil waterway. A white house is positioned near the water's edge, surrounded by trees and a clear blue sky. The peaceful setting is enhanced by the gentle reflection of the landscape in the water.
Home in Oxford

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

FamilyValueWalkability

4.99 out of 5 average rating, 100 reviews
Top Guest favourite
A red barn-style building is positioned on a lush green lawn, surrounded by trees and residential structures. A porch is visible on the upper level, and a colorful wheel mural decorates the front. A gravel path leads to the entrance.
Guesthouse in Cambridge

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.

FamilyValueDecor

4.99 out of 5 average rating, 126 reviews
Guest favourite
A well-appointed bedroom features a wooden bed with soft green linens and decorative pillows. A bedside table with drawers holds a vintage clock and a decorative object. A woven light fixture hangs above, and natural light filters through the window covered by blinds.
Home in Salisbury

Stella

Welcome to Stella! She has been lovingly restored by our family and carefully designed by our son who owns JoonMoon Design with his beautiful wife. We are a family who loves to travel and discover places of rest. Stella was designed with that in mind. She is approachable, comfortable and invites you to kick off your shoes and relax. She is walking distance to Salisbury University and close to many restaurants and stores.

ValueLocationIndoor spaces

4.9 out of 5 average rating, 148 reviews
Guest favourite
A bright and inviting room features two pink armchairs with a small table between them, set against a backdrop of light walls and hardwood flooring. An elegant chandelier hangs from the ceiling, while a vintage-style dresser and a decorative fireplace enhance the space's charm.
Home in Cambridge

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.

LocationFamilyDecor

4.89 out of 5 average rating, 122 reviews
Guest favourite
A tranquil pond is framed by natural stone, featuring a gentle waterfall surrounded by lush greenery. Bright flowering plants and a manicured lawn lead to a serene outdoor seating area overlooking the water, offering a peaceful retreat in nature.
Home in Salisbury

Highbanks House

Forget your worries in this spacious and serene space. Welcome to your dream home! This stunning 5-bedroom, 3-full-bath rancher is nestled on over 6 acres of private land, offering a perfect blend of comfort and nature. Located just 6 miles from downtown Salisbury and 8 miles from Salisbury University, this property provides both tranquility and convenience.

FamilyValueKitchen

4.83 out of 5 average rating, 183 reviews
Guest favourite
A classic three-story home features a navy blue exterior with white trim. A welcoming front porch is furnished with multiple rocking chairs, offering a comfortable space to relax. Decorative details include a distinctive turquoise front door, complemented by white support columns and a well-maintained lawn.
Home in Cambridge

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.

LocationValueWi-Fi

4.95 out of 5 average rating, 287 reviews

Popular amenities for holiday rentals near Layton's Chance Vineyard and Winery

KitchenWi-FiPoolFree parking on premisesAir conditioning

Condo rentals with Wi-Fi

Top Guest favourite
A panoramic view of the ocean is visible, with gentle waves lapping at the sandy beach. Below, an outdoor pool is surrounded by lounge chairs and clear pathways, providing a peaceful atmosphere. Skies are blue, enhancing the serene coastal setting.
Condo in Ocean City

Oceanfront Condo w/ Resort Amenities 3BDR &3pools

LocationFamilyComfort

4.89 out of 5 average rating, 148 reviews
Top Guest favourite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Condo in Ocean City

Gorgeous Beachfront! King Bed, Direct Ocean View!

FamilyLocationLong stay

4.99 out of 5 average rating, 157 reviews
Guest favourite
Condo in Ocean City

White Marlin 107 Renovated Amazing Bay Views Pool

ValueLocationPool

4.89 out of 5 average rating, 126 reviews
Top Guest favourite
A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.
Condo in Rehoboth Beach

Renovated Condo Near Outlets, 3.5 Miles to Beach

LocationFamilyBeach

4.98 out of 5 average rating, 226 reviews
Top Guest favourite
A two-story condo is presented with light-colored siding and large windows adorned with sheer curtains. A coral front door welcomes guests, complemented by a small staircase leading to the upper level. A private balcony with white railings is visible above the entrance.
Condo in Lewes

Lewes Beach Vibes

ValueLocationOutdoor spaces

4.98 out of 5 average rating, 110 reviews
Guest favourite
A spacious living area features a cozy arrangement of seating with patterned upholstery and soft textures. A circular coffee table is centered amidst the furniture, and a wall-mounted television is paired with a stone accent wall. Large sliding doors open to the private balcony.
Condo in Ocean City

Beach Paradise 202-Downtown Luxury Condo Bay View

LocationValueKitchen

4.91 out of 5 average rating, 201 reviews
Top Guest favourite
A spacious living area features two large sofas, one being a queen sleeper bed. A wooden coffee table sits on a neutral area rug. A dresser and smart TV are positioned along the wall, with a dining area visible through an open layout.
Condo in Rehoboth Beach

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach

LocationValueComfort

5.0 out of 5 average rating, 131 reviews
Guest favourite
The living area features soft blue furnishings and a light wood coffee table. Floor-to-ceiling windows offer direct views of the ocean, while two lamps provide warm lighting. A coastal-themed artwork adorns the wall, enhancing the serene atmosphere of the space.
Condo in Ocean City

Direct Oceanfront with a View and Amenities Galore

FamilyLocationPool

4.94 out of 5 average rating, 341 reviews

Family-friendly house rentals

Top Guest favourite
A two-story farmhouse with a light blue exterior features white trim and is complemented by a welcoming front porch. Rocking chairs are positioned on the porch, surrounded by colorful flower beds and lush green grass. Mature trees provide partial shade, enhancing the outdoor setting.
Home in Church Creek

Church Creek Charm (Close to Blackwater!)

FamilyLocationCleanliness

4.97 out of 5 average rating, 174 reviews
Top Guest favourite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

FamilyLocationKitchen

4.96 out of 5 average rating, 140 reviews
Top Guest favourite
Home in Cambridge

Waterfront, Private Pier, Sleeps 10, 4 bedrooms

FamilyValuePool

4.98 out of 5 average rating, 154 reviews
Top Guest favourite
An aerial view captures a sprawling, waterfront property surrounded by lush greenery. The modern home sits prominently on a well-manicured lawn, leading to a serene bay. The driveway winds through tall trees, with clear blue water visible in the background.
Home in Cambridge

Osprey's Retreat Waterfront w/ private beach/dock

LocationFamilyComfort

4.97 out of 5 average rating, 118 reviews
Top Guest favourite
The exterior of the home is showcased with a well-maintained lawn, framed by flowering shrubs. A welcoming front porch is visible, featuring two wooden benches. The entrance is highlighted by a maroon door, accompanied by classic shutters on the windows.
Home in Parsonsburg

Charming Home in a Neighborhood

FamilyLocationIndoor spaces

4.99 out of 5 average rating, 184 reviews
Top Guest favourite
A comfortable living room features plush seating arrangements, including reclining chairs and a spacious sofa. A coffee table sits in the center, complemented by a large television mounted above a brick fireplace. Bookshelves filled with titles line the walls, adding a cozy touch.
Home in Easton

4 bdrm, 3 bath, 2,700 sqft whole house on 1 acre

LocationValueAir conditioning

4.97 out of 5 average rating, 104 reviews
Top Guest favourite
The inviting exterior of the house showcases a covered front porch with two rocking chairs. A well-maintained lawn and shrubbery frame the entrance, while a gravel driveway leads to a detached garage in the background. The setting reflects a serene neighborhood atmosphere.
Home in Salisbury

Salisbury Hideaway

LocationValueAccess

4.99 out of 5 average rating, 134 reviews
Superhost
The exterior of a single-story home is showcased, featuring a light-colored facade with a front porch and white railings. A manicured lawn and several trees are visible, creating a serene atmosphere. A paved driveway leads up to the house, while dark rain clouds suggest a potential rainstorm.
Home in Seaford

Cozy home in Seaford

FamilyLocationCheckout

4.89 out of 5 average rating, 120 reviews

Apartment rentals with air conditioning

Top Guest favourite
A bright dining area features a wooden table surrounded by four chairs, illuminated by natural light from the sliding glass doors. A cozy armchair with a soft throw blanket is present, with a clock and decorative art pieces on the walls, creating a welcoming atmosphere.
Apartment in Church Creek

Nature's Rest in Church Creek

LocationValueView

4.97 out of 5 average rating, 453 reviews
Top Guest favourite
The exterior of the guesthouse is characterized by a light gray facade and two garage doors, framed by planters with green foliage. The enclosed yard is secured by white fencing, creating a private outdoor space.
Apartment in Salisbury

Cozy Guesthouse | Full Kitchen + Private Patio

FamilyLocationOutdoor spaces

4.94 out of 5 average rating, 249 reviews
Guest favourite
A cozy living area features a dark leather sofa and two blue chairs arranged around a round coffee table. Soft lighting is provided by stylish lamps on both ends. Framed artwork lines the walls, and natural light streams through the curtains.
Apartment in Cambridge

Little Slice of Cambridge. 2 bedroom, pet friendly

ValueFamilyParking

4.91 out of 5 average rating, 160 reviews
Guest favourite
A spacious driveway leads to the entrance of a one-bedroom apartment. The light-colored building features a pair of windows flanking a central door. A large, open grassy area extends beyond the driveway, bordered by trees in the background.
Apartment in Salisbury

Private Luxurious One Bedroom Apartment

ValueFamilySleep quality

4.91 out of 5 average rating, 207 reviews
Top Guest favourite
Apartment in Cambridge

Pint-Sized on Poplar | Across the Street from RAR

LocationIndoor spacesParking

5.0 out of 5 average rating, 31 reviews
Guest favourite
A spacious wooden dining table is centrally positioned, adorned with a vase of fresh flowers. The kitchen area is visible in the background, featuring cabinetry and modern appliances. Exposed beams add character to the ceiling, enhancing the open feel of the loft.
Apartment in Cambridge

Station House East: Upscale Loft in Cambridge, MD

LocationParkingBathroom

4.91 out of 5 average rating, 22 reviews
Guest favourite
A modern living area features a light-colored sectional sofa alongside a dark blue armchair. A round coffee table displays a decorative item, while a bright kitchen with stainless steel appliances is visible in the background. Natural light enters through large windows, enhancing the openness of the space.
Apartment in Seaford

Apartment in Seaford, DE

LocationHospitalityNearby

4.98 out of 5 average rating, 46 reviews
Superhost
Apartment in Laurel

New, Large 2 Bedroom Apartment - Central Laurel

FamilyValueIndoor spaces

4.8 out of 5 average rating, 5 reviews

Other great holiday rentals near Layton's Chance Vineyard and Winery

Top Guest favourite
The exterior entrance of a converted corn crib features natural wood siding and a gabled roof. Large double doors framed by lantern-style lights open into a welcoming space, complemented by potted plants on either side. Lush green trees and a gravel path are visible in the surrounding landscape.
Guesthouse in Easton

Chill in The Crib! Easton, Maryland

FamilyLocationBathroom

4.99 out of 5 average rating, 659 reviews
Top Guest favourite
A spacious living area features a comfortable sofa adorned with decorative pillows. A dining area with wooden chairs is visible, alongside a kitchenette equipped with appliances. Natural light floods the room through large glass doors, while decorative blue and white accents enhance the atmosphere.
Farm stay in Madison

Madison Nature Getaway

LocationFamilyWalkability

4.98 out of 5 average rating, 229 reviews
Guest favourite
A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.
Cottage in Deal Island

Private Beachfront Cottage with 2 Bedrooms + Loft

LocationFamilyView

4.94 out of 5 average rating, 100 reviews
Guest favourite
Tiny home in Cambridge

Blackwater Tiny Cabin on Snakehead Creek

FamilyValueSleep quality

4.89 out of 5 average rating, 704 reviews
Top Guest favourite
An aerial view captures the waterfront home surrounded by lush greenery and a circular driveway. The expansive water body in the background reflects the sky, while a dock is visible along the shoreline, enhancing the serene landscape.
Home in Cambridge

Magical Waterfront Home Dock, Firepit, Family Fun!

ValueFamilyNearby

5.0 out of 5 average rating, 55 reviews
Top Guest favourite
Home in Church Creek

Blackwater Sika Deer & Wildlife Retreat

LocationFamilyQuiet

5.0 out of 5 average rating, 17 reviews
Top Guest favourite
Home in Cambridge

Relaxing Retreat on the Hudson

ValueLocationKitchen

4.96 out of 5 average rating, 84 reviews
Top Guest favourite
Cottage in Galestown

Cozy Millpond Cottage • Fall Getaway

LocationValueIndoor spaces

4.96 out of 5 average rating, 24 reviews