Vacation Rentals By Owner In Cumberland, MD

Welcome to this delightful apartment in Cumberland. This charming space features 2 bedrooms, one with a king bed and the second with two full beds, perfect for a small group of guests. The bathroom is equipped with a shower for your convenience. Enjoy the tremendous amenities such as AC, heating, washing machine and dryer, fully equipped kitchen, and WiFi during your stay. Perfect for bikers, we have installed a bike rack under a roof to keep your bikes safe and dry. This unit is located on the 2nd level, with no elevator -- you must be able to do stairs. We hope you enjoy what our place and Cumberland has to offer.brbrWhether you are just passing through, staying for work or vacation, or visiting with friends and/or family let this cozy space be where you can relax and recharge.brbrThis location is steps away from downtown for dining, shopping, galleries, and entertainment. Just down the street is George Washington's headquarters during the French and Indian War, and the hillside which is now home to the Emanuel Episcopal Church was the original Fort Cumberland. Up the street is the very popular Basecamp Coffee Shop. brbrCumberland is the end point of the Chesapeake and Ohio Canal and Towpath and the beginning of the Great Allegheny Passage. Both trails are just steps away from Greene Street as well as the Potomac River. brbrAlso conveniently located near the interstate for easy access to Rocky Gap State Park and Casino Resort, Green Ridge State Park, and nearby LaVale and Frostburg for additional shopping, dining and entertainment options. In less than than an hour drive away is all the year round outdoor recreational activities surrounding Deep Creek Lake.

Charming 2-bedroom apartment with equipped kitchen and AC, in Cumberland, MD.

Cumberland, Maryland, United States

Bed

Bath

Sleeps

$318.4

Welcome to our private cabin tucked away on 12 acres of woodland in Western Maryland. If you are looking for a secluded getaway but still want to be close to restaurants and other attractions, Brice Hollow Getaway is worth considering!brbr***Please read the entire description including our weekend reservation policy.***brbr As of 2023, we gutted the cabin and did a complete remodel including new windows, doors, roof, and expanded the deck. brThe fully equipped kitchen has granite countertops, dishwasher, full range, microwave, Keurig & regular coffeepots, toaster, blender, and fridge/freezer. brThe living room has a propane fireplace and Roku TV. We are in remote enough location that cable TV is not available but you are able to stream movies on the smart TV through the WIFI that is available. br Cell phone service is limited but the cabin is equipped with Starlink internet to provide an dependable online connection. br The bedroom is equipped with a queen size bed and has dimmable lights to add to the romantic atmosphere. There is an exterior door in the bedroom that leads to the hot tub on the deck. br You will love the spacious bathroom with a large window that allows a lot of natural light in. The walk in shower is large enough for two people and has a regular shower head as well as a rain head! The soaking tub is not your average tub. It is equipped with hydrotherapy jets. Instead of having a water pump that circulates water through a couple jets, the tub has a couple hundred small ports inside the tub that heated air is blown through. The full body massage that it gives you is very relaxing! You can adjust the intensity of the “bubble massage” to your taste. The air that is blown through the ports is heated which means that your water will not cool off while you enjoy a long soak. br While the cabin is geared for a romantic getaway for two people, the open loft which overlooks the kitchen and living room is equipped with a couch and full-size bed. The extra bed allows you to bring your children or share the cabin with another couple. br There is a washer and dryer available for use in the laundry room.br The front porch wraps around the side of the cabin and connects to the large deck in the back. There is a propane grill on the deck outside the kitchen door. Enjoy relaxing in the large hot tub while you watch the sun go down through the trees and listen to the crickets as they sing their night songs.br Off the deck, there is a fire ring to enjoy campfires. Firewood is complimentary with your stay. br The surrounding area has a lot to offer whether you are looking for food, restaurants, shopping, or outdoor activities. The C&O Canal Towpath which goes from Cumberland, MD to Washington DC has a trail head at Spring Gap just two miles away that provides a great place for biking and walking. Enjoy the local mountains while riding on a steam powered train on the Western Maryland Scenic Railroad. There are lots of hiking options in the nearby Green Ridge Forest. If you enjoy canoeing/kayaking, the Potomac River is nearby and provides some leisure paddling. br The minimum stay over the weekends is two nights. br In order to allow the house keepers a day off for church and family, we will give you Sunday night at half price if you are staying Friday and Saturday night. br For your safety and protection, there is a Ring door bell/camera on the front door. There are no other cameras on the property. br We want to help your stay be as relaxing and rejuvenating as possible. If you need anything during your stay, please let us know. We live nearby and will do our best to make your stay at Brice Hollow Getaway a positive experience!

Cabin

Secluded, romantic cabin with hot tub on 12 acres of woodland.

Cumberland, Maryland, United States

Bed

Bath

Sleeps

$124.71

Experience Cumberland like a local in this 1-bedroom home. The fabulous space features a king bed in the bedroom and a cozy living room with a sofa bed, perfect for extra guests. One full and one half bathrooms offer convenience. Guests enjoy a comfortable atmosphere with heating and air conditioning throughout. Whether relaxing after a day of exploring or preparing a meal in the well-appointed kitchen, this enchanting city house feels like a true home away from home. Experience what Cumberland has to offer with a stay at our wonderful home….”Centre of the City”.

Beautiful 1-bedroom home in charming Cumberland. Convenient downtown location.

Cumberland, Maryland, United States

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Bath

Sleeps

$218.38

Welcome to The Whistle Stop — a beautifully restored historic home in the heart of Cumberland, Maryland. Designed with comfort, charm, and relaxation in mind, this spacious getaway offers the perfect blend of farmhouse elegance and modern convenience for families, couples, groups, and adventure seekers alike.brbrProperty Highlights:br• 4 beautifully designed bedroomsbr• Sleeps up to 8 guests comfortablybr• 2 full bathroomsbr– One with a relaxing bathtubbr– One with a modern stand-up showerbr• Fully equipped kitchenbr• Cozy dining and gathering spacesbr• Laundry area with washer & dryerbr• Stylish farmhouse-inspired décor throughoutbr• Smart TVs & WiFibr• Peaceful atmosphere perfect for relaxing after a day of exploringbrbrPrime Cumberland Location:brThe Whistle Stop is conveniently located close to all of Cumberland’s top attractions while still offering a quiet, cozy retreat feel.brbrNearby attractions include:br• Downtown Cumberland Historic Districtbr• Western Maryland Scenic Railroadbr• C&O Canal Towpathbr• Great Allegheny Passage (GAP Trail)br• Rocky Gap State Park & Casinobr• Shops, coffee houses, breweries & local restaurantsbr• Allegany Museumbr• Historic train station & canal areabrbr Deep Creek Lake & Outdoor Adventures:brJust a scenic drive away from Deep Creek Lake, guests can enjoy:br• Boating & kayakingbr• Fishingbr• Hiking & waterfallsbr• Wisp Resort skiing & snow tubingbr• Mountain coaster & adventure activitiesbr• Beautiful lakefront dining and shoppingbrbrWhether you’re planning a relaxing weekend, family vacation, girls trip, couples getaway, hiking adventure, or railroad-themed stay, The Whistle Stop offers a warm and inviting home base to experience everything Western Maryland has to offer.brbrWe can’t wait to host you at The Whistle Stop!

The Whistle Stop a historic home in the heart of Cumberland, Maryland

Cumberland, Maryland, United States

Bed

Bath

Sleeps

$126.12

Your Cumberland adventure begins at this 2-bedroom apartment. Inside, guests find a queen bed and a full bed, perfect for a comfortable night's rest. The bathroom features a refreshing shower and a handy hair dryer. Whether you’re relaxing indoors or getting ready for the day, the space offers excellent comfort with heating and air conditioning. This awesome apartment creates a cozy, inviting atmosphere that makes every stay feel special. We look forward to hosting you at our place.

The Suite On Smallwood

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(9)

$148.4

After a year of complete renovation of the house, we invite you to visit a 122-year-old house that fully meets modern housing standards. We installed an advanced smart home system that controls lights, blinds, heating and air conditioning and even helps you rate your sleep quality and listen to your favorite music. For your culinary masterpieces, there is a full kitchen with all the necessary equipment and a basic set of spices.brbrYou will get the part of the duplex, but nobody is living in the other side. you will be alone at the property during the booking.brbrPlease, absolutely No smoking in the property and No pets allowed.

The Dacha. Cumberland vacation

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(16)

$157.34

Welcome to our Cozy, Rustic 1st floor apartment in a quiet duplex off Hambright's Alley. Walkable to historic downtown Cumberland & the C&O Canal & GAP Trail! Explore local attractions or take day trips to Luray Caverns(VA), Smithsonian Museums(DC), or the world's largest Bicycle Museum(PA) all within 2 hours.brbr Our place is perfect for any stay - pleasure, festivals, work, or just passing through. Enjoy the GAP trail and more outdoor adventures! We have everything you need for a comfy stay. Let us know if you need kid accommodations. brbrHistoric 1910 building with modern updates. Spacious queen bedroom. Kitchen with unique antique island perfect for meals. In-unit laundry with free detergent for your convenience. Cyclists are welcome to bring the bikes into the hallway. brbrOur space comfortably fits 2, with an extra comfy twin bed (sheets included) that can be set up in the living room or bedroom. Perfect for a small family!brbrFUR BABIES ARE WELCOMED!!brbr Important: We are committed to protecting our properties and keeping up-to-date with short-term rental regulations, which is why you might be asked to complete our independent verification. Before your stay begins, you may need to complete a verification process using our 3rd party verification which includes the payment of a nominal fee for damage waiver or a security deposit.

Relaxing Rustic Oasis - 6 min walk to Downtown! Cyclist Welcomed & Pet friendly!

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(8)

$152.72

Welcome to our Comfy & Cozy 2nd floor apartment in a quiet duplex off Hambright's Alley. Walkable to historic downtown Cumberland & the C&O Canal & GAP Trail! Explore local attractions or take day trips to Luray Caverns(VA), Smithsonian Museums(DC), or the world's largest Bicycle Museum(PA) all within 2 hours.brbr Our place is perfect for any stay - pleasure, festivals, work, or just passing through. Enjoy the GAP trail and more outdoor adventures! We have everything you need for a comfy stay. Let us know if you need kid accommodations. brbrHistoric 1910 building with modern updates. Spacious queen bedroom. Kitchen with unique antique island perfect for meals. Enjoy playing Pac-Man and Galaga on the arcade game. In-unit laundry with free detergent for your convenience.brbrOur space comfortably fits 2, with an extra comfy twin bed (sheets included) that can be set up in the living room or bedroom. Also includes a comfy sofa to bring total guest count up to 4. Perfect for a small family!brbr Important: We are committed to protecting our properties and keeping up-to-date with short-term rental regulations, which is why you might be asked to complete our independent verification. Before your stay begins, you may need to complete a verification process using our 3rd party verification which includes the payment of a nominal fee for damage waiver or a security deposit.

Relaxing Rustic Oasis II - 6 min walk to Downtown! Cyclist Welcomed!

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$316.95

Relax and explore Cumberland from our cozy duplex! This charming home offers comfort and amenities for everyone. It features two bedrooms (two queen beds, two cribs), two full kitchens, and two living rooms with a twin bed in each. Enjoy all the comforts of home, including laundry, AC, and WiFi. Perfect for pleasure, work, or exploring the GAP trail.brbrImportant: Guest verification and a security deposit/damage waiver may be required via a third-party service.

Rustic Oasis for the Family - 6 min walk to Downtown

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(25)

$307.8

Enjoy the beautiful woodland and hillside! Peace & quiet with the North Branch of the Potomac River across Rt 51 (walking or bicycling distance!). Canoeing, kayaking, on the Potomac River - just across the road! Bicycling on the C&O Canal Tow Path (Spring Gap Mile Post 173.3) is also just across the road. brThe house includes a Trex deck to enjoy the lovely outdoors. Large gourmet kitchen with Jenn Air range and coffee bar. All bedrooms, bathrooms, and living areas are spacious! Living room has gas fireplace insert and large Smart TV for cozy relaxation. Rec Room offers a Foosball Table with freestanding gas stove. Twenty minutes from historic downtown Cumberland and just across the Potomac River from West Virginia. Two sets of sliding glass doors onto deck from the Living Room. Sliding glass doors onto large deck from Primary Bedroom. Large deck across entire front of the house. brProperty includes outdoor security cameras (we have a wide range of wildlife on the property).brEnjoy the home and lovely surroundings with all the region has to offer!

Woodland Oasis - Quick access to the Potomac River and the C&O Canal Tow Path!

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(56)

$132.5

Large 2 bedroom unit located on the second floor. It is located in a safe quiet neighborhood less then a mile to downtown, GAP, and C&O Canal trails and restaurants. Guests will enjoy their own private apartment to include 2 bedrooms, full kitchen, bath, living area, porch and a private entrance. We do not have cable TV however we do have WIFI, 40 TV, Roku, ( Netflix, Prime, Disney Plus and Hulu ) DVD player, movies' games and books for adults and children. Street level secured bike storage on premises as well.

Private 2 Bedroom Apt with bike storage 1 mile to the GAP and C&O Canal /

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(1)

$119.77

Welcome to this adorable apartment in Cumberland. Guests will find a cozy space featuring one bedroom with a queen bed, perfect for a restful night. The apartment offers both heating and air conditioning, ensuring comfort no matter the season. A clean, well-kept bathroom adds convenience to your stay. Whether you're here for a quick getaway or an extended visit, this terrific spot provides a relaxing retreat. We hope you'll enjoy your stay at our apartment.

Adorable 1-bedroom apartment with AC in charming Cumberland

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(5)

$127.2

Experience the best of Cumberland from this serene 2-bedroom retreat. Perfectly situated for outdoor enthusiasts and relaxation seekers alike, our space serves as the ultimate home base just moments from the GAP Trail. After a day of adventure, unwind in one of two plush queen-sized beds designed for a restful night's sleep. Whether you're here to cycle the trails or explore historic downtown, this cozy apartment offers the perfect blend of comfort and convenience.

Tranquil 2-Bedroom Retreat: Modern Comfort, Fast Wi-Fi & Near GAP Trail

Cumberland, Maryland, United States

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Bath

Sleeps

$91.13

Get ready to relax in this 1-bedroom apartment in Cumberland. The space features a queen bed that promises a soothing night’s sleep. Guests enjoy a brilliant bathroom with a refreshing shower and a hair dryer for convenience. Climate control keeps the apartment comfortable with both heating and AC. Whether you’re unwinding after a day of exploring or simply enjoying some quiet time, this amazing spot offers a cozy retreat. You’re sure to make fantastic memories with a stay at our place.

Fantastic 1-bedroom apartment in charming Cumberland

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(13)

$222.6

Please have all guest read below before requesting a booking and turn your app notifications on for easy communication with host. Thank you!brbrWhen booking please do the following so we can accept reservation quickly:brbr1. Let us know what brings you to beautiful western Maryland and what state you are traveling frombr2. Confirm all guest will respect our simple house rules brbrWe are excited for you to come relax and feel at home on this unique property which backs up to 70,000 acres of peaceful forest filled with wildlife. brbrOur mountain home provides:brbr- a cozy three bedroom, one level house with 2 full bathrooms and full kitchenbr- 1 queen bed, 4 twin bedsbr- a front yard, covered porch, back deck and grillbr- free high speed internet and large Roku TVbr- AC for summertimebrbr**House rules and policies:brbr- Check in is between 4pm – 8 pm, check out is by 10ambr- Children are welcome and must be with an adult at all times; rental is not child proofbr- Due to allergy concerns animals are not allowedbr- Maximum number of guest is 6, must include booking guest, all must provide ID at or before check in for key code to be obtainedbr- Past the deck and all woods surrounding rental are off limit to guestbr- Only those on reservation, the original day of booking, and only guest vehicle are allowed to enter property, driveway and house during staybr- Please refrain from loud noise, smoking/vaping, operating hand tools, charging vehicles, drugs, glitter, parties or reunionsbr- No trespassing past deck of house or in surrounding woodsbr or turning your vehicle around in any area past deck for any reasonbr- Please park near house parking signbrbrOccasionally, during the day you may hear lawnmowers, machinery, hunting, dirt bike riding or caretaker tending to wood stove or utilities in basement should the need arise.brbr**Guest failure to respect house rules and policies may result in cancellation of reservation by VRBO, a fee, or both. Thank youbrfor your consideration.

Clean & Private Mountain Home

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(28)

$137.64

In the delightful town of Cumberland, you'll find our cozy two-bedroom cottage, ideal for your upcoming getaway. As you step inside, you'll be greeted by a cozy living room, where you can unwind and enjoy the smart TV. The fully stocked kitchen is a chef's delight, equipped with a stove, oven, refrigerator, grill, and all the necessary appliances to prepare delicious meals. Gather around the dining table and savor your culinary creations, or step outside and fire up the grill for an al fresco dining experience.brbrWhen it's time to relax, head to the porch and soak in the peaceful atmosphere, or gather around the fire pit and roast marshmallows under the stars. For those seeking adventure, the Downtown Cumberland Historic District and the Western Maryland Railroad Station are just a short 14-minute drive away, offering a glimpse into the region's rich history. The C&O Canal is very near for hiking or biking.brbrThroughout your stay, you'll enjoy the convenience of free WiFi, as well as access to a variety of games and books for both adults and children. And after a day of exploration, unwind in the soothing hot tub, letting your worries melt away. Whether you're seeking a cozy getaway or a family-friendly vacation, our 2-bedroom cottage in Cumberland has everything you need for an unforgettable experience.

Cottage

2-bedroom cottage 14 minutes from Downtown Cumberland Historic District

CUMBERLAND, Maryland, United States

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Bath

Sleeps

$199.5

Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom 4 bath house. There is a large gathering room with a fully furnished kitchen and full bath downstairs. There are 5 bedrooms , 3 Bathrooms and a Sitting room upstairs. There is a 12’x25’ Covered Patio at the rear of the house. This house is located on 40 acres along the C&O Canal Trail, Knobley Mountain Tunnel, and the North branch of the Potomac River. It is only 1 mile from The Great Allegheny Passage Trail. Be sure to take The River Walk to Pebble Beach on the property. It has 2 river Islands with 2 miles of river frontage. It is only 1 mile from Canal Place in down town Cumberland MD. and 5 miles from the Rocky Gap Casino and Resort. Bring your Motorhome, Camper, or tent, we have a lot of room for Camping. There is also a Campground located on the Property that Guest can also enjoy. The property has Fishing, Boating, Kayaking, Cycling, Hiking, and R&R. Rent for 2 Days, Week-end, or Week . Only $185.00 a Night for 3 Guests. Extra Guests over 3 are $50.00 per guest per night. Children under 6 are Free. If you are bringing Pets (cats dogs) they must be keep in the down stairs 6’x9’ side entry room. Pets are permitted out side leashed or unleashed. Thanks Donelly br

Awesome New Property/ CANAL RIVER RETREAT

Cumberland, Maryland, United States

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Bath

Sleeps

$192.92

Are you looking to get away and relax in a peaceful country setting, in beautiful Western Maryland Mountains, this is the place for you. Relax and Enjoy our cozy cottage a little quiet, two bedroom one and a half bath house. Nest it on just over an acre of ground enjoy our beautiful back deck. Just outside of Historic Cumberland, Maryland and a mile from 68 and a little over three minutes from Historic Downtown Cumberland, Maryland, we are also close to the scenic Railroad, C&O Canal towpath and The Great Allegheny passage

Cozy Cottage 2 bedroom house one and half bathrooms Cumberland, Md with AC, WiFi

Cumberland, Maryland, United States

Bed

Bath

Sleeps

Exceptional(4)

$106.16