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

Chalet in Davis

4.85 out of 5 average rating, 156 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 in Mercersburg

4.94 out of 5 average rating, 105 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.

Superhost

Home in Oakland

4.83 out of 5 average rating, 6 reviews

New: The Absolute Cutest Cabin in Deep.Creek

Blue Cork Cabin is the cutest cabin in Deep Creek Lake! This lakefront cottage has been updated with modern features and a cheerful, beautiful interior to be the perfect intimate escape! Thoughtful art galleries, beautiful displays, and curated book collections chase you from room-to-room, making it a space you'll want to thoroughly explore. Outside the home, you'll find an array of amenities designed to help you get the most of your Deep Creek experience. On the deck, you'll find a comfortable

Guest favourite

Townhouse in Champion

4.91 out of 5 average rating, 132 reviews

Seven Springs Sunridge year-round mountain chalet!

Sleeps 13 Ski in/Ski out walking distance to the slopes! Renovated 3 bed 3.5 bath townhouse with loft! Chalet boasts 2 king, 1 queen, 4 twin and a queen sleeper couch. Twin beds may be pushed together to make 2 full beds. Includes access to a private hot tub, outdoor kitchen, outdoor dining area and two patios! Best slopes in Western PA. There is a 24 hour shuttle provided to the main lodge. There are tons of biking/hiking trails, golf and a pool in the summer. Have fun in the sun and snow!

Guest favourite

Home in McHenry

4.9 out of 5 average rating, 127 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!

Superhost

Home in Hidden Valley

5 out of 5 average rating, 3 reviews

Kepple Castle by Camp Hope

This condo is fit for royalty. It has everything you need and more. It’s renovated and impeccably decorated, but more importantly is the location. It’s convenient to everything. You can hop on the skipped in two minutes or enjoy the golf, pool, pickleball, tennis and biking trails less than one minute away. It’s the perfect spot. Once you stay here you won’t want to leave. As a bonus, your host grew up here and knows all of the fun adventure places to visit and dining in the area. Book now!

Guest favourite

Home in Hagerstown

4.93 out of 5 average rating, 57 reviews

Hot tub, Pool table+darts, near ski resorts

Your family will be close to everything when you stay at this centrally-located place. Quiet neighborhood and comfortable settings ** NO PARTIES ** Plenty of room to enjoy a getaway with friends and family without the headache of inconveniences. Basketball hoops on the driveway and pool side. Dart board and pool table offer indoor activities when the weather doesn't want to cooperate. Multiple HD t.v's for your viewing pleasure and HDMI connections to connect a gaming console of your choice.

Guest favourite

Townhouse in Somerset

4.93 out of 5 average rating, 187 reviews

Charming Getaway Hidden Valley 4BR+3Bath Hot Tub

4-Bedroom Hidden Valley Townhouse w/ back deck and private hot tub overlooking pond! Turnkey, furnished and ready for you to make it your very own mountain getaway. Kitchen remodeled and new flooring throughout! 2 bedrooms on main floor w/ full bathroom. Master bedroom upstairs with private balcony overlooking pond. 2nd suite upstairs with separate full bathroom. Enjoy relaxing on back deck that overlooks the pond; within walking distance to the South Ridge Center Pool & Playground.

Guest favourite

Home in Swanton

4.93 out of 5 average rating, 15 reviews

Renovated Home w/Dock, Stunning Views, 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.

Superhost

Cabin in Harpers Ferry

4.8 out of 5 average rating, 420 reviews

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!

Superhost

Home in Hidden Valley

4.92 out of 5 average rating, 116 reviews

Luxury Retreat in mountains Blow out rates

Luxurious ski in/out home.Hidden Valley is a four-season resort. This is the perfect destination for family festivities, getaways, and retreats.Our home can house the bride or grooms family for a wedding weekend.All furniture and mattress are brand new for 2019.towels and Bedding Included.Hot tub .Ski RoomFully equipped gourmet kitchen with granite counter tops. and Washer/Dryer. WIFI access, Cable.Pool Table.Foosball Tabel Ample ParkingWrap around deck.

Guest favourite

Apartment in Oakland

4.91 out of 5 average rating, 76 reviews

Top Notch Lake Getaway - Cozy in a plush resort

Complete remodel and upgrades in Nov 2022. Unique space and a great getaway; 2 separate sleeping areas. Spacious +BR w/loft nestled on the shores of Deep Creek Lake, professionally furnished w/onsite mgmt, King bed in private bedroom w/closet, Queen bed in loft area, propane fireplace, kitchenette with microwave & full size fridge, keurig, full bath lower level, vaulted ceilings and much more. Community fitness center. Please, 25yo to rent.