Holiday rentals in Chestnut Ridge

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Top-rated holiday rentals in Chestnut Ridge

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Superhost

Cottage in Hidden Valley

4.88 out of 5 average rating, 101 reviews

RENOVATED! Top location ON lake! Walk to slopes!

This newly renovated, spacious "farmhouse theme" cottage is in an amazing location ON Lake George & a 3 minute walk to the base of the slopes & restaurants / Glaciers Pub. The new remodel had large/multiple families in mind with the design including a "kids suite bunk room" that has 6 beds & bath plus a huge sectional sofa, TV, gaming table and plenty of entertainment. The large deck and fire pit overlook the lake making this a truly unique year round destination home. *7 miles to 7 Springs!

Top guest favourite

Townhouse in McHenry

5 out of 5 average rating, 39 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

Flat in South Side Flats

5 out of 5 average rating, 8 reviews

Wow! Skyline Sunset Escape On Hackstown

Ahoj and welcome to your elegant 2-bed, 1.5-bath home with breathtaking downtown views! Newly renovated with a thoughtfully designed interior, this home offers a distinctive experience. Enjoy parking in a 2-car garage plus an outdoor space, and easy access to downtown and Oakland. Featured on the South Side Historic Homes Tour, it’s a true Pittsburgh gem. Pets are allowed! Relax on the deck with a fire pit, or unwind by the custom mosaic fireplace with a 55” TV or in the luxurious soaking tub.

Guest favourite

Townhouse in Champion

4.92 out of 5 average rating, 147 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!

Top guest favourite

Apartment in Champion

4.99 out of 5 average rating, 105 reviews

Seven Springs 2 Bedroom Condo

Newly renovated charming mountain getaway located in the beautiful community of Swiss Mountain within Seven Springs resort. Minutes to the ski slopes, restaurants, bars, lodge, golf & resort activities. Free shuttle to the resort & a short walk to the pool and tennis. Whether you ski, golf or just want to relax by the pool, this condo has everything. Well equipped kitchen, sleeps 4-6 comfortably. King bed in the master, twin daybed and trundle in second bedroom, & 2 queen sleeper sofas.

Guest favourite

Townhouse in McHenry

4.95 out of 5 average rating, 21 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

Home in Swanton

4.94 out of 5 average rating, 18 reviews

Renovated Home with Dock, HotTub, Golf 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 Swanton

4.79 out of 5 average rating, 92 reviews

"Whispering Pines"

Soft greens and powder blues adorn the interior and blend seamlessly with the lush natural setting of "Whispering Pines." The home is conveniently located within minutes of the State Park and could be the perfect place to gather for your next family vacation destination! You’ll love my place because of the views, the location, the ambiance, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Superhost

Chalet in Oakland

4.91 out of 5 average rating, 128 reviews

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!

Guest favourite

Townhouse in Seven Springs

4.96 out of 5 average rating, 27 reviews

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.

Guest favourite

Apartment in Oakland

4.91 out of 5 average rating, 79 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.

Superhost

Cabin in Oakland

4.93 out of 5 average rating, 221 reviews

Lakehound Lodge - lake view, pet friendly

Cozy cabin in the middle of all that Deep Creek Lake area has to offer! Enjoy a dip in the hot tub by the fire with peekaboo lake views under twinkle lights. This three level cabin boasts a bedroom and bathroom on each level, two wood burning fireplaces, two living rooms, and an enclosed side porch with hot tub. Pets welcome for a fee. Close to the lake, Wisp, parks, golfing, fishing, and much more! Follow insta @lakehoundlodge