Holiday rentals in Oldtown

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.

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

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.

Tequila Sunset, Harpers Ferry. Entire first floor!

Welcome to Tequila Sunset in Harpers Ferry, WV! This beautiful, secluded home has stunning sunset views, you'll truly feel on top of the world! 100 mile vista of the gorgeous Blue Ridge Mountains. Entire first floor is yours, no shared spaces! Over 1200 SF of room to unplug & relax. King size Nectar bed, cozy indoor wood burning fireplace, outdoor firepit, 84" TV, & a private deck to enjoy the natural surroundings. Just 2 miles from the renowned Mountain Lake Club and the Appalachian Trail!

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!

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.

Spectacular Chalet, Timroc II, close to lake, Wisp

ENJOY every season!! Short walk to the lake and dock! ! 15 minute drive to Ski Wisp! Fire pit, decks and screened in porch! Relax in the hot tub, enjoy family and/ or friends time and just get away from it all! 5 comfortable sized bdrms, each with large windows letting in natural daylight. First floor master, hardwood flooring throughout, many sliders for easy access. Finished bsmt with pool table, separate bdrm, full bath and laundry! DON'T SEE YOUR DATE, PLEASE CALL!

Cozy Cabin Hidden Away on a Lake!

MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

Southwinds Ultimate Slope Side Relaxation Spot

Welcome to the ultimate relaxation spot! This Townhouse in the Southwind’s community blends luxury, location, and all the amenities necessary for a perfect vacation. The townhouse is luxuriously outfitted so every guest has the chance to truly relax in comfort. The townhouse is located so close to the action that the ski lift nearly flies over the deck. This spot blends thrill and tranquility, making it perfect destination for unforgettable memories.