Holiday rentals with outdoor seating in Cumberland

Guesthouse in Grantsville

An open living space features wooden beams overhead and warm brown flooring. A cozy seating area is paired with a light-colored sofa. A Christmas tree adds a festive touch, while a kitchenette with cabinetry is visible in the background, accompanied by a dining table and chairs.

4.95 out of 5 average rating, 178 reviews

“The Loft” Guest House w/wifi workspace, gym etc

This unique two story guest house has a style all its own. The Loft has one bedroom upstairs along with a great workspace with excellent WIFI, full size bathroom and closet and a small kitchenette including microwave, fridge, air fryer and Keurig. Room darkening curtains, AC, TV w/Roku, full bath/shower unit, pullout sofa and queen size bed all in a very large and open floor plan! The first floor is set up as a gym/workout room. Ample and easy parking. Use of the outdoor patio area. Adults only.

A Cape Cod style cottage is depicted, featuring a porch with a sloped roof and a welcoming entrance. The surrounding yard is green, bordered by neatly trimmed shrubs. In the background, rolling hills are visible, providing a natural setting.

4.93 out of 5 average rating, 273 reviews

Jacob's Cottage

Free WI-FI now available. Our place is good for couples, solo adventurers, business travelers and families (with kids). The Cottage is a quaint, Cape Cod style house built in 1950. It sits high on a hill in the heart of Maryland's Appalachian Mountains in Allegany County. It is surrounded by views of Wills Mountain and Shrivers Ridge. The Cottage sits amongst a 660 acre family managed forest. Visitors have spotted deer, turkey, rabbits, squirrels, black bear and a multitude of song birds.

5 out of 5 average rating, 126 reviews

NEW LISTING-"Cumberland Cottage"-charming,quaint

Relax in this charming, renovated rancher in a peaceful setting. Located outside of the city limits but convenient to attractions and dining. This home is comfy with all the amenities you have in your own home. Outside area for your children to play or for you to relax on the back porch. Cumberland is in easy driving distance to PA and WV. Enjoy cooking together and dining or playing games in the dining room, then relaxing in the living area. Renovated but still keeping the charm of a rancher.

4.78 out of 5 average rating, 171 reviews

A cozy seating area features a light-colored sofa, complemented by a red accent pillow. A glass coffee table is positioned nearby, with a round dining table and four white chairs visible in the background. The kitchenette area is furnished with essential appliances and wall art is displayed on the whitewashed walls.

Apartment in Cumberland

The Caverne'-quaint EFF near C&O Canal, GAP & UPMC

This special place is close to everything Cumberland offers making it easy to plan your visit. Just minutes via bike to GAP and C&O Canal. This serviced apartment includes all the amenities a hotel room offers but with privacy and extra space. Off street parking is just steps away from the space where amenities include coin operated laundry & soda machine. Free wifi, tv, full size refrigerator, coffee maker with coffee etc provided, and micro & toaster oven for quick snacks or simple meals.

4.92 out of 5 average rating, 316 reviews

An aerial view captures the cottage nestled among vibrant autumn foliage, surrounded by colorful trees. The serene pond reflects the rich hues of fall, while solar panels are visible on the cottage roof. A winding dirt road leads to the property, enhancing the secluded atmosphere.

Home in Clearville

Grouseland's Pondside Vacation Cottage

Set about a quarter mile of the road, our pet friendly solar powered vacation cottage is a perfect getaway for anyone trying to spend some alone time with nature! Guests have complete privacy inside the cottage with a full kitchen, two TV's, Wi-Fi, and a mini split system for heating and cooling. As well as exclusive access to the hot tub, fire pit and pond outside! We also have various shared hiking trails through the woods surrounding the cottage for campers and cottage guests to enjoy!

The exterior entryway features a set of stairs leading to a porch with white railing and overhead lighting. A small bush is visible beside the stairs, and the brick façade of the home provides a warm appearance, enhanced by the nighttime ambiance.

4.94 out of 5 average rating, 105 reviews

Great Location, Spacious, Comfy 2 bdrm 3 bed home

This home is centrally located near all things fun and exciting to do in Cumberland. Situated in a quiet residential neighborhood in the Western Maryland mountains. Minutes from historic downtown, the Potomac River, Rocky Gap State Park, Pennsylvania, the University of Pittsburg Medical Center, the C &O canal and much more. This home features 3 queen beds, 2 bedrooms both with 55" TV's and blackout curtains, a large separate dining room, a spacious kitchen, and living room with a 65" TV.

4.97 out of 5 average rating, 234 reviews

A cozy living area features a spacious sectional sofa adorned with a colorful throw. Natural light streams through multiple windows, illuminating the warm beige walls and soft carpet. An antique wooden table and a vintage chair add character to the inviting space.

Apartment in Meyersdale

Country Home

Relax with family, friends, or enjoy a solo retreat at this peaceful place to stay in the country. Chestnut House was built in the early 1940s, with Wormy Chestnut wood everywhere! It is a unique home, with an apartment built over a garage / wood working shop.. then connected to the main house later. This space available to rent is separate and fully functional from the main house where we live. Enjoy 2 bedrooms, 1 bathroom, full kitchen and living area.. along with the large outdoors!

4.99 out of 5 average rating, 192 reviews

A blue cottage is illuminated at night, showcasing distinct architectural features including gabled roofs and decorative trim. The background reveals a sprawling view of the city lights, creating a contrast against the dark sky. Trees and greenery frame the scene, enhancing the serene atmosphere.

Cottage in Cumberland

The Cottage on the Hill

Nestled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in one of your reserved spaces and step down to a unique retreat high above the city to enjoy a vintage cottage with modern amenities. Walk to Historic Cumberland, enjoy local and regional attractions, or stay in and grill, build a fire, or play pool, poker, board or yard games. Well appointed, fully equipped, and with a beautiful view, come relax and enjoy this one of a kind location.

4.94 out of 5 average rating, 233 reviews

A charming two-story house is surrounded by well-tended gardens, featuring a gravel driveway leading up to the front porch. The exterior is painted in a soft gray hue, complemented by large windows that offer opportunities for natural light.

Home in Frostburg

Country Home Near Main St. & Trail

Welcome to this charming and cozy home sitting at the highest point in Frostburg. Incredible mountain and forest views from the upstairs windows, lots of old house details and including two staircases and a sleeping porch. There are hardwood floors throughout. Lots of space to relax. Two full baths, one with shower and one with tub/shower. Gas range and fully stocked kitchen. Smart TV's in two bedrooms, and in the main living room. Strong Wifi, and a washer and dryer in the basement.

4.98 out of 5 average rating, 111 reviews

The cottage is nestled among vibrant autumn foliage along the riverfront. A rock cliff rises behind it, while a winding path leads to the house, which is surrounded by a mix of colorful trees. The serene river can be seen nearby.

Cottage in Green Spring

The River House

A cozy, spacious and private get away with access to entire finished house. Located river front of the South Branch of the Potomac River, giving it the best view in the area. This cottage is also within 3 miles of C&O Canal, 17 miles from Historical Romney, 15 miles to Cumberland, MD and 10 miles to the Paw Paw, WV tunnel. 2 kayaks and 1 canoe available for river excursions. Come enjoy hiking, biking, kayaking, fishing or simply soak in all nature has to offer in the backyard.

A charming outdoor seating area features two intricately designed white wicker chairs with floral cushions and a small table. Soft string lights enhance the space, while a lush green view is visible in the background through the open area.

4.91 out of 5 average rating, 137 reviews

Queen City Quarters- cozy, historic, 1920s home

Stay in a quiet setting as you explore Cumberland, MD. Enjoy a day trip on the nearby, scenic, steam train. Bike the Gap and C&O trail, minutes away. Explore the restored historic downtown with shopping and restaurants. This space is not suitable for small children or those with mobility concerns. No large groups or parties. Bedroom doors are louvered doors. See pictures. Research city and area if you are unfamiliar with economic conditions. We have a bike rack for 3 bikes.

4.86 out of 5 average rating, 325 reviews

A modern kitchen features light gray cabinetry with an island centerpiece. Stainless steel appliances, including an oven and refrigerator, are complemented by a colorful bowl display. A detailed wall graphic provides helpful kitchen rules, while ample counter space offers convenience for meal preparation.

Home in Frostburg

Allegany Connection

NOTICE: extra santizing of hand touching areas in place for your protection. This eclectic 2-story duplex, late 18th century structure has both old and new charm. Single BR & bath upstairs; LR and Kit downstairs. Only 1 block from Main St. restaurants & unique shops. All are welcomed. Please bring your own infant bed. Sorry no pets. Free reserved parking for 1 vehicle & fast Wi-Fi. Instant booking is on. ABSOLUTELY NO SMOKING, or any kind is permitted inside our home.

Popular amenities for Cumberland outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

4.99 out of 5 average rating, 109 reviews

A serene exterior view of Everlong showcases the inviting front deck surrounded by lush greenery. The wooden railing and steps lead to a comfortably designed patio space, framed by trees that highlight the home's natural setting.

Home in Berkeley Springs

Everlong ~ Pet-friendly Retreat on 2 Wooded Acres

4.99 out of 5 average rating, 143 reviews

A single-story blue house is set against a backdrop of leafy trees. The front porch features a welcoming red door and two outdoor chairs. Soft landscaping surrounds the house, which has a neatly maintained lawn and a paved driveway leading to the entrance.

Home in Romney

Southern Charm Getaway in Romney, WV - Sleeps 6

4.94 out of 5 average rating, 156 reviews

The cabin is illuminated at night, showcasing its rustic charm among surrounding trees. Warm lights accentuate the porch and pathway, enhancing the inviting atmosphere. The outdoor space is highlighted by well-placed rocks and greenery, creating a serene outdoor retreat.

Home in High View

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing

4.98 out of 5 average rating, 144 reviews

A single-story house is depicted surrounded by lush green trees, set against a backdrop of rolling hills. The exterior features a metal roof and a front porch, with a driveway leading to a garage. A spacious yard is visible, providing a serene countryside setting.

Home in Artemas

Rines' Country Getaway

4.9 out of 5 average rating, 262 reviews

The exterior of a single-family house is shown, featuring a light gray facade and a welcoming yellow front door. An American flag flutters above the steps, which are bordered by colorful flower pots. A well-maintained lawn complements the inviting entrance.

Home in Meyersdale

Our House on the GAP Bike Trail

4.93 out of 5 average rating, 107 reviews

A well-equipped kitchen features wooden cabinetry and an island with seating for four. Natural light fills the space, highlighting the polished wood floors. A full-size refrigerator, stove, and microwave are visible, along with counter appliances and a window offering an outdoor view.

Home in Markleton

The Country Ranch

4.94 out of 5 average rating, 104 reviews

A comfortable living space features a teal accent wall and a large sectional sofa, complemented by a cozy area rug. A wooden media console holds a television, while a colorful artwork and shelves filled with books add character to the room.

Home in Confluence

Flanigan Farmhouse - Cozy, modern 3 bdr on 4 acres

4.98 out of 5 average rating, 117 reviews

A stone fireplace rises from the floor to the ceiling, flanked by two large windows adorned with sheer curtains. A simple wooden coffee table rests on a light-colored area rug, while a flat-screen TV is positioned nearby on a wooden stand, creating a cozy living space.

Home in Berkeley Springs

Our Shangri La

Apartment rentals with outdoor seating

5 out of 5 average rating, 131 reviews

A spacious living area features a large leather sectional sofa with accent pillows, paired with rustic wooden coffee tables. A sleek entertainment center holds a wall-mounted TV, while framed landscape artwork adorns the walls, adding a touch of color to the room.

Apartment in Accident

The Nest near Deep Creek

Apartment in Friendsville

The kitchen features white cabinetry and modern appliances, including a stove and refrigerator. A wooden bar with stools offers a casual dining space. Natural light enters through the door leading outside, illuminating the warm wood accents on the walls and floor.

4.95 out of 5 average rating, 174 reviews

Riverview Suite

4.84 out of 5 average rating, 44 reviews

Apartment in Cumberland

Downtown Rustic Oasis II - Cyclists Welcome!

Apartment in Berkeley Springs

A well-appointed outdoor space features a private cedar barrel sauna, complemented by a small dining table with two yellow chairs. Greenery surrounds the area, and a patterned outdoor rug adds texture to the wooden deck, creating a relaxing environment for guests.

5 out of 5 average rating, 92 reviews

The Downtown Flat at Creekside

5 out of 5 average rating, 77 reviews

The studio apartment features a compact kitchen with white cabinetry and stainless-steel appliances. A dining table with two wooden chairs is positioned beside a cozy seating area, which includes a striped armchair. Natural light fills the space, highlighting the warm hardwood flooring.

Apartment in Bedford

Private Studio Apartment - Own Entry

4.91 out of 5 average rating, 226 reviews

The living room features two fold-down sofas and a coffee table, positioned on a colorful area rug. A unique antler chandelier hangs from the ceiling, and decorative wall art, including maps, enhances the rustic feel. Natural light enters through the nearby doors.

Apartment in Confluence

Turkeyfoot Wisteria Apartment

4.89 out of 5 average rating, 197 reviews

A cozy living area features a dark sectional couch adorned with decorative pillows. A large flat-screen TV is mounted on the wall, while wooden accents define the space. A dining area with wooden chairs is positioned at the bar counter, creating a warm and inviting setting.

Apartment in Rockwood

Rustic Ranch Guest Apartment

Superhost

The bedroom features a spacious bed with neutral bedding and a wooden headboard. Two lamps provide soft lighting, while a fan hangs overhead. A small table and chair are positioned nearby, with a textured area rug covering the wooden floor. Large windows allow natural light to enter.

Apartment in Oakland

4.67 out of 5 average rating, 21 reviews

Charming 1-bdrm with balcony, Close to Everything.

Condo rentals with outdoor seating

A cozy living area features large windows that provide expansive views of the outside scenery. Comfortable seating includes a light-colored sofa and a lounge chair. A coffee table sits in the middle, while a television is mounted on the wall above a wood-burning fireplace.

Condo in Oakland

4.25 out of 5 average rating, 89 reviews

Charming 3BR Lakeview | Deck | Hot tub | W/D

5 out of 5 average rating, 6 reviews

A charming log home exterior is displayed, featuring a combination of brown wood siding and stone accents. A spacious driveway leads to the entrance, complemented by landscaped areas with greenery. The surrounding trees and blue sky enhance the inviting atmosphere of this ski retreat.

Condo in McHenry

Top of The Slopes- 4 bdrm, Ski in/Ski out, Hot Tub

4.95 out of 5 average rating, 146 reviews

A two-story condo building is shown against a clear blue sky, surrounded by well-maintained greenery. The parking area in front features designated spaces, with vehicles parked nearby. Trees provide shade, enhancing the inviting atmosphere of the community.

Condo in McHenry

Lake Access/2BR/2Bath/kitchen/pool/5m to Wisp

An expansive covered deck features a seating area with white chairs and a table, surrounded by panoramic views of the historic town. A grill and a fire pit are visible, while planters with greenery add a natural touch to the inviting outdoor space.

Condo in Cumberland

4.73 out of 5 average rating, 11 reviews

Romantic condo with a view in historic Cumberland

The exterior of the condo is presented, featuring a dark blue wooden facade and light blue shutters. A white door provides entrance, surrounded by greenery and small shrubs. A concrete pathway leads to two chairs and a small table positioned in front.

Condo in Paw Paw

4.38 out of 5 average rating, 13 reviews

Avalon Resort (Clothing Optional) Paw Paw WV Condo

A cozy living area features vaulted wooden ceilings and a stone fireplace, accompanied by a wooden coffee table. Natural light fills the space through multiple windows, while a Pacman arcade machine adds a playful touch to the ambiance.

Condo in Oakland

4.31 out of 5 average rating, 133 reviews

Renovated 1BR Lakeview | Balcony

Condo in McHenry

1 Mi to Wisp Resort: Hot Tub Haven in McHenry!