Holiday rentals in Cumberland

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Top-rated holiday rentals in Cumberland

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Guest favourite

Home in Cumberland

4.93 out of 5 average rating, 56 reviews

Great Location, Spacious, Comfy 2 bdrm 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 2 bedrooms with queen size beds both with 55" TV's and blackout curtains, a large separate dining room, a spacious kitchen, and living room with a 65" TV.

7–14 Sep

€ 137 per night

Guest favourite

Flat in Cumberland

4.95 out of 5 average rating, 109 reviews

The Dove's Nest w/no cleaning fees

The Dove's Nest features a fully equipped chefs kitchen , dishwasher, washer and dryer, plenty of parking and a large private patio with bike parking. Easily accessible from I-68 and ideally located in a comfortable part of town. Less than 1 mile from the University of Pittsburgh Medical Center (UPMC), Allegany College of MD and the Constitution Park. A quick 2 miles to historic downtown Cumberland where the C & O Canal meets the Great Allegheny Passage. Perfect location for hiking and biking.

26 Sep – 3 Oct

€ 95 per night

Guest favourite

Home in Cumberland

4.94 out of 5 average rating, 207 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.

4–11 Nov

€ 107 per night

Guest favourite

Loft in Cumberland

4.94 out of 5 average rating, 36 reviews

Historical loft, 2 Blocks from Trail & Downtown

When you enter your loft apartment you will have an interior space to secure your bikes. After a fun day on the C&O or GAP trail you will enjoy a shower, a cup of local Basecamp coffee, and restful sleep Conveniently located 2 blocks off a trail entrance. Downtown restaurants only a 5 minute drive Included in your room is a kitchen sink, microwave, fridge/freezer, toaster and 12 cup coffee pot with local Basecamp coffee in regular & decaf, & tea Keyless entry, entire place to yourself

3–10 Nov

€ 77 per night

Guest favourite

Flat in Cumberland

4.84 out of 5 average rating, 294 reviews

WOW! Rustic-Modern Apt - PETS WELCOME!

Quaint and comfy one bedroom apartment located just one block from historic downtown cumberland. It is in a safe and quiet neighborhood. The Cumberland Theatre & Western Maryland Scenic Railroad, the C&O Canal and GAP Trail are just around the corner. We are pet friendly (one-time per pet fee applies, billed after booking) but we do a deep clean after each guest, you’d never know that pets have ever been hosted. AT THIS TIME, WE ARE UNABLE TO ACCOMMODATE EARLY CHECK-IN/OUT DUE TO COVID.

20–27 Sep

€ 151 per night

Guest favourite

Flat in Cumberland

4.99 out of 5 average rating, 318 reviews

Steeple View Flat in Historic District

Relax in your first level flat. Entire private efficiency suite with a secure self check in. The entrance located along side of the main house in Cumberland’s Historic District. You can safely park your car and walk to many of Cumberlands amenities. If you’re biking, they can be stored inside. Canal Place has unique shops a winery and a bike rental facility. Cumberland theater is adjacent to the property, also Baltimore St. Promenade offers a delicious choice of indoor and outdoor dining.

24 Sep – 1 Oct

€ 103 per night

Guest favourite

Home in Cumberland

4.83 out of 5 average rating, 144 reviews

Charming 1907 Home in Historic Downtown Cumberland

This charming 1907 home is located just blocks from the main pedestrian street in Historic Downtown Cumberland and a 10 minute walk from Canal Place, the C&O Canal Great Allegheny bike trails, and the Western Maryland Scenic Railroad. The remodeled interior is equipped with all the modern conveniences, including a large kitchen and bathroom with jacuzzi tub and seven-head shower. The house maintains its historic charm with exposed brick and has a balcony, back patio, and yard space.

26 Apr – 3 May

€ 119 per night

Guest favourite

Home in Frostburg

4.93 out of 5 average rating, 205 reviews

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.

25 Dec – 1 Jan

€ 131 per night

Guest favourite

Flat in Frostburg

4.89 out of 5 average rating, 124 reviews

The GreyLoo

Cozy, clean and friendly downstairs apartment. Stocked with all the things you need for a short stay as well as the long haul. Close to the Great Allegheny Passage, Main Street Frostburg, Frostburg State University, the Frostburg Pool, and many other locations. Located 33 mi from Wisp Resort/Deep Creek Lake and 18 mi from Rocky Gap Casino Resort. Just a few miles from I68. Enjoy this cozy place and bring your furry friends. Lots of nearby hiking, biking, and outdoor adventures.

2–9 Oct

€ 83 per night

Guest favourite

Home in Cumberland

4.9 out of 5 average rating, 457 reviews

Cumberland Street House -GAP trail perfection!

Cyclists dream come true! The Cumberland Street House is less than a quarter mile from the Great Allegheny Passage - perfect for large groups! All of Cumberland's charm within walking distance. Downtown restaurants and shops only a half a mile away. Historic district, Cumberland Theatre & Western Maryland Scenic Railroad are just around the corner. Bikes can easily be stowed in the back room off the kitchen. Easy parking, and fenced-in yard is great for kids and pooches.

17–24 Feb

€ 144 per night

Superhost

Cabin in Fort Ashby

4.87 out of 5 average rating, 99 reviews

Hilltop Cabin Retreat - Secluded & cozy - Wi-Fi!

The Sonny Side Hilltop 10-acre Cabin is the perfect secluded getaway to unwind and enjoy nature. Spend quality time with friends/family, explore the outdoors, ATV trails, or hunt with appropriate tags - contact for more details. My father (Sonny) built this cabin in 2004 with his own two hands. It was his primary residence until passing from cancer at my sister's home in Maryland in 2019. We would like to share this lovely cabin with guests to help offset costs. Please Enjoy!

15–22 May

€ 150 per night

Guest favourite

Cottage in Cumberland

4.99 out of 5 average rating, 167 reviews

The Cottage on the Hill

Snuggled against a hillside, at the end of a small city lane, sits a charming private retreat. Park in your private space, walk down to a unique retreat high above the city and 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.

8–15 Sep

€ 183 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Cumberland holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cumberland's top sights

Western Maryland Scenic Railroad19 locals recommend

Puccini Restaurant8 locals recommend

Crabby Pig6 locals recommend

El Jinete3 locals recommend

Cafe Mark11 locals recommend

Queen City Creamery, Cafe & Deli14 locals recommend

Other great holiday rentals in Cumberland

Guest favourite

Home in Cumberland

4.86 out of 5 average rating, 29 reviews

Cozy Cottage

6–13 Feb

€ 129 per night

Guest favourite

Home in Cumberland

5.0 out of 5 average rating, 8 reviews

Spacious Parkside Oasis!

6–13 May

€ 123 per night

Guest favourite

Home in Cumberland

5.0 out of 5 average rating, 12 reviews

Charming Home Near Downtown

20–27 Oct

€ 123 per night

Guest favourite

Home in Cumberland

4.95 out of 5 average rating, 22 reviews

WiggerZen

27 Jan – 3 Feb

€ 154 per night

Superhost

Home in Cumberland

4.85 out of 5 average rating, 52 reviews

Queen City Quarters- cozy, historic, 1920s home

12–19 Dec

€ 151 per night

Guest favourite

Home in Cumberland

5.0 out of 5 average rating, 65 reviews

NEW LISTING-"Cumberland Cottage"-charming,quaint

7–14 Oct

€ 160 per night

Guest favourite

Cabin in Springfield

4.97 out of 5 average rating, 73 reviews

Secluded 2 BR cabin in the forest awaits you!

15–22 May

€ 130 per night

Superhost

Flat in Cumberland

5.0 out of 5 average rating, 8 reviews

Mountain View Paradise

8–15 Aug

€ 106 per night

Show all

Quick stats about holiday rentals in Cumberland

Total rentals	60 properties
Rentals with dedicated workspaces	40 properties have a dedicated workspace
Pet-friendly rentals	10 properties allow pets
Family-friendly rentals	30 properties are a good fit for families
Total number of reviews	4K reviews
Nightly prices starting at	€ 38 before taxes and fees

Holiday rentals in Cumberland

Top-rated holiday rentals in Cumberland

Home in Cumberland

Flat in Cumberland

Home in Cumberland

Loft in Cumberland

Flat in Cumberland

Flat in Cumberland

Home in Cumberland

Home in Frostburg

Flat in Frostburg

Home in Cumberland

Cabin in Fort Ashby

Cottage in Cumberland

Holiday rentals for every style

Cottages

Cabins

Houses

Popular amenities for Cumberland holiday rentals

Stay near Cumberland's top sights

Other great holiday rentals in Cumberland

Home in Cumberland

Home in Cumberland

Home in Cumberland

Home in Cumberland

Home in Cumberland

Home in Cumberland

Cabin in Springfield

Flat in Cumberland

Quick stats about holiday rentals in Cumberland

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore