Holiday rentals in Oldtown

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Top-rated holiday rentals in Oldtown

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Townhouse

5 out of 5 average rating, 33 reviews

Our Lovely Lake Retreat

Spacious 3 bedroom, 2.5 bath townhome with gorgeous views of Deep Creek Lake and WISP ski slopes. The newly updated townhome sleeps 8 comfortably. You will enjoy the air conditioning, fully equipped kitchen & grill, wood burning fireplace and 4 smart TV's. 15 steps up to entrance. Neighborhood amenities: indoor community pool, picnic tables, dock and a beach/sand area (kids will love). Level lakefront access right across the street. Min age to rent 25. Max 3 cars. HOA rule: no trailers/campers.

Guest favourite

Chalet

4.85 out of 5 average rating, 158 reviews

Big, Bright SLOPESIDE Ski Chalet, Outdoor Hot Tub!

Don't be fooled by other misleading "slopeside" listings! This gorgeous 5-bedroom lodge is adjacent to Timberline's Winterset ski run — perfect for families. Outdoor hot tub. Large open floor plan, plus separate living area downstairs. Two gas fireplaces. Master suite has Jacuzzi for 2. Wifi, 2 flatscreen HDTVs. Please don't request to book this chalet unless you have at least 3 positive reviews on Airbnb. If you don't have 3 positive reviews, your request to book will be respectfully declined

Guest favourite

Chalet

4.94 out of 5 average rating, 108 reviews

Amazing Whitetail Ski Holiday and Mountain Retreat

Welcome to our beloved Mountain home. Located at Whitetail resort you can walk to the slopes and enjoy the après ski in our beautiful cozy house with cabin feel. Perfect ski holiday, weekend getaway, or place to work remotely with high-speed internet. Only 1.5 hours from DC & Baltimore. This is the perfect place to escape the city, connect with nature and recharge. A place to build up fond memories. All season adventures, enjoy skiing, swimming, hiking, golfing, fishing, lakes and local farms.

Guest favourite

Place to stay

5 out of 5 average rating, 32 reviews

Unique A Frame: Hot Tub, Fire Pit, Cold Plunge

Step into this luxurious 3BR 2BA, A-Frame cabin built in 2024 and nestled in the tranquil area of Berkeley Springs, WV. Lounge in the stylish and radiant interior, soak in the hot tub on the deck, or explore "America's First Spa" and many Appalachian attractions and landmarks! ✔ Deck w/Hot Tub ✔ Fire Pit ✔ Cold Plunge ✔ Outdoor Dining ✔ Green Egg ✔ 3 King Bedrooms ✔ Open Design Living + Loft ✔ Full Kitchen ✔ Office ✔ Smart TV ✔ Wi-Fi ✔ Parking ✔ Community Pool, Tennis & Trails See more below!

Guest favourite

Home

4.99 out of 5 average rating, 120 reviews

Southern Charm Getaway in Romney, WV - Sleeps 6

Beautiful, comfortable & clean family friendly getaway in West Virginia's first town! Located in the center of town and walking distance to restaurants, public library, boutiques, shopping, historical sites, Civil War trenches, public pool and Visitor's Center. Just a few short miles to The Potomac Eagle Scenic Excursion Train & to the South Branch of the Potomac River for fishing and canoeing. You will find many day trip activities within an hours' distance, including Skiing, hiking &biking

Superhost

Cabin

4.97 out of 5 average rating, 65 reviews

Centrally Located | Mountain View | Private 1 Acre

Red Run Retreat is the perfect getaway cottage whether you are hiking through Swallow Falls Park, skiing down Wisp Resort Trails or boating on Deep Creek Lake, this is the place for you! Private one acre. Enjoy your morning cup of coffee while watching the sunrise on the front porch, BBQ and entertain friends on the spacious back deck and unwind around the firepit in the front yard. You will certainly feel at home. Take on exciting adventures and make new memories at this affordable cottage.

Guest favourite

Home

4.9 out of 5 average rating, 130 reviews

Ski/in Ski/out Luxury Home Voted #1

For Summer or Winter---The Best House and LOCATION in Deep Creek Lake- Large level lawn with a sandy beach. Private dock slip. Views on both sides- across street from chairlift. Watch your family and friends ski and ride down the mountain from the glass enclosed 45' x25' open great room at the party lodge located at base of chair 5. Luxury with gourmet kitchen.- lots of room for parties. 70" flat screen, two wet bars, pool table, three indoor Jacuzzis, hot tub, fire pit--- many extras!

Guest favourite

Townhouse

4.93 out of 5 average rating, 14 reviews

Villa Celeste - Deep Creek Lake, MD

This well-maintained condo has lake and mountain views! Catch amazing sunsets nightly from the deck bar! Two of the 4 bedrooms are primary suites, one on the main level and one on the upper level. With almost 2500 square feet there is room for everyone and amenities galore. Conveniently located to everything Deep Creek has to offer. It's less than a quarter mile from multiple restaurants, shopping & marinas. Love to ski or play golf? It's less than 2 miles to Wisp Ski & Golf Resort.

Guest favourite

Cabin

4.92 out of 5 average rating, 61 reviews

SuperBOWL weekend OPEN~Close to town~Brewery HIKE

Welcome to TreeTOP Breeze, our amazing cabin that will make you feel like you are in a TREE HOUSE. Our modern cabin is perfect for gathering your large friend or family groups! Two private wooded acres, this gem features 4 spacious bedrooms with the most comfy beds, 4 full baths, a private hot tub, 2 cozy fireplaces, a DOUBLE DECKER screened in porch. Only 5 miles to downtown Berkeley Springs, WV—ranked the #9 Small Town in America-it’s the perfect place to relax, unwind, and explore!

Guest favourite

Home

4.94 out of 5 average rating, 16 reviews

Renovated Home,10 mins to WISP, HotTub DogFriendly

Recently renovated, this beautiful home sits on a hillside in the Waterfront Greens community. Stunning views, privacy, great location, and many amenities make it the perfect choice. The new deck has plenty of seating & some of the best views around. Waterfront Greens offers a par 3 golf course, mini golf, tennis, lake access and the dock area. One of the best locations in the area for safely walking & riding bikes. Please note that there is a pet fee (for up to 2 dogs) of $200.

Guest favourite

Home

4.97 out of 5 average rating, 35 reviews

Mins to Ski, High Speed Internet, Luxury Cabin

Mins to Ski Resorts, Downtown Davis and all Major tourist destination, 4 Seasons Vacation home, Resort style with some amenities. 4 beautiful BR, 3 Ba, Spacious family room with wood cathedral ceiling, DR open to the kitchen and living room area, large floor to ceiling fireplace is the perfect area to snuggle up with your family, large deck, patio, 2 large master bedrooms. This is the perfect house to bring your entire family. Lots of natural lights, jetted jacuzzi,

Superhost

Home

4.73 out of 5 average rating, 11 reviews

Memories Too

Escape the hustle and bustle of everyday life and come stay in our 3 bedroom vacation rental condo in McHenry, Maryland! Enjoy the stunning lake view and relax in the hot tub after a day of skiing at the nearby ski resort. Our house is the perfect place to unwind and take in the beauty of nature. Come experience the ultimate in relaxation and comfort! Your family will be close to everything when you stay at this centrally-located place. Reserve your stay today!.