Holiday rentals in Overlook Mountain

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Top-rated holiday rentals in Overlook Mountain

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

Guest favourite

Guest house in Bearsville

4.98 out of 5 average rating, 561 reviews

Mt. Guardian Guest House Exquisite Mountain Views

Exquisite mountain views, immaculate cleanliness, cozy wood stove, beautifully designed, great bed, all amenities, freshly roasted coffee, well-equipped kitchen, excellent Wi-Fi, cable TV, Netflix, and serenity! Close to everything, far from everyone. AirBnB PLUS, Super Hosts, registered with town and county. We follow AirBnB Covid cleaning protocols and run a large HEPA air filter between guests. Pet friendly with prior permission. Over 500 exceptional reviews–many guests return again and again. Winter mid-week discount: book 3 or more nights (Sunday - Thursday) and get one night free! Our little cabin is made and furnished with great care and attention to detail. The space is comfortable and homey, bright and flooded with fresh mountain air. Many of the pieces are hand made and those that are not were chosen for both their aesthetic and functionality. We offer high speed internet access, full service internet TV, Netflix, and a full kitchen with every utensil and pot/pan you need (we've been to a bunch of airbnb's and we hardly ever saw a decent sized spaghetti pot!) and hand crafted bathroom with shower. The views from every window are exquisite - from the front we have miles and miles of national park that change in appearance every day. Whether its covered in fog, changing leaves, bright sunshine or fresh snow Mount Guardian delivers a constantly changing and stunning landscape. Enjoy your morning cup from one of the hammock chairs, the couch, or with a newspaper at the kitchen table... At night , forego the tech and curl up in front of the fire with one of our books, or set up a board game with a glass of wine. The place is cozy warm in the coldest months, and although we have air conditioning, its rare that you'll need it. When you're ready - jump into our queen sized memory foam bed before deciding to get one for yourself (yes - its that good and we're happy to share the details). and gaze up through the skylight at the stars. If you're used to sleeping with constant light and noise you'll be amazed at how well rested you feel after just a couple nights on the mountain. Skiers- we can't guarantee the snow, but the cabin is 20 miles from Hunter, 31 miles to Windham, and 36 miles to Belleayre. Inquire about our mid-week skier specials (Sunday night through Friday morning). We are pet friendly, but only small and medium sized dogs (sorry, we can't allow cats). We charge a cash deposit on arrival, and return it to you at the end of your stay. If you would like to bring a dog, PLEASE SEND AN INQUIRY (DO NOT USE INSTANT BOOKING). We have some pet guidelines which you need to read and agree to first. Nothing huge or surprising, but due to some irresponsible pet owners, we like to be clear before you book. If you are planning to come by motorcycle, PLEASE send an inquiry (do not use instant booking). Special Events in the area: June: Taste of Country and Mountain Jam at Hunter Mountain (Both are great by the way!) June through October: Usually something just about every weekend. Check out what is going on at Levon Helm Studios, Bearsville Theatre, the Colony, Maverick Concerts. Many other music and theater venues a little farther off. Mid October: The view of the changing leaves is spectacular Mid October: Woodstock Film Festival. Book early. This brings big crowds to our little town. Late October: Woodstock Luthier Festival November: Halloween in Woodstock is an event not to be missed. Half for the kids, half for all the folks around here who haven't abandoned their 8 year old. A LOT of fun. Christmas: when Santa comes to Woodstock, most of the town turns out for the welcome party. Like no other. We use a keypad system so you can check-in any time after 3:00pm. If you're coming from the city by bus (Trailways stops in Bearsville and Woodstock), you can get an Uber, Lyft, or a cab- but service can be pretty slow up here (there are only a few drivers.) The cabin is a good 45 minute walk from town, up a pretty good hill. We are generally nearby if you need anything. We also leave very explicit instructions for reaching us if there is an urgent need. The cottage is set in the secluded woods of Mt. Guardian, four miles from the center of Woodstock. Explore artist workshops and colonies, excellent music venues, great restaurants, bars, and plenty of cool little shops. Hiking, skiing, swimming, and tubing are all nearby. Licensed massage therapist available next door or in cabin (please book in advance). It's beautiful up here every season- spring and fall are magical, summer swimming, tubing, exploring and winter skiing and times by the fire. Around here it helps to have a car. Though you can do without one if you're staying in for the most part, the cabs in Woodstock are from Kingston and charge a rather serious call out fee. Uber/Lyft are now available, but you may wait a while to be picked up. As mentioned before Trailways bus service will drop you in Bearsville or Woodstock from the Port Authority and the Amtrak drops in Rhinecliff. Cabs are available at Rhinecliff station but your best bet is to rent a car or drive your own. In winter, the roads up here are plowed frequently. Our driveway is plowed and level, and is accessible to most vehicles throughout the year. We have a dog who lives on the property (next door) - he's very gentle and doesn't bark unless a critter alerts him - though we have a fair few of those up on the mountain! He is an indoor dog and unless you are around while he's being walked or chasing sticks, his presence shouldn't impact your stay. With prior approval, we are happy to welcome quiet well-mannered pets. We require an additional security deposit and provide a receipt and simple "pet deposit agreement" on check-in. We ask pet owners to follow our "pet rules" which include keeping your dog in a suitable pen if you are gone from the cabin. No pups on furniture or bed, pick up after your dog in the yard. You may want to bring a mat or blanket. We will provide full details regarding pets when we get your inquiry. You'll have good wifi in the cabin. Mobile service is great for Verizon, and very limited for other carriers.

11–18 Jun

€ 172 per night
Guest favourite

Home in Woodstock

4.91 out of 5 average rating, 634 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

9–16 Feb

€ 132 per night
Guest favourite

Home in Woodstock

4.93 out of 5 average rating, 262 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic view through timber-framed picture windows. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve, as well as the attention to architectural detail, is unique.

11–18 Jul

€ 726 per night

Popular amenities for Overlook Mountain holiday rentals

Other great holiday rentals in Overlook Mountain

Guest favourite

Cabin in Kingston

4.98 out of 5 average rating, 332 reviews

Come Stay in "The Shoe"

14–21 Nov

€ 133 per night
Guest favourite

Apartment in Lanesville

4.97 out of 5 average rating, 540 reviews

Stylish Condo Ski on/ Ski off Hunter Mountain

18–23 Apr

€ 121 per night
Guest favourite

Treehouse in Willow

4.96 out of 5 average rating, 703 reviews

Willow Treehouse - secluded, unique, romantic

28 Jan – 4 Feb

€ 438 per night
Guest favourite

Bungalow in Saugerties

4.88 out of 5 average rating, 185 reviews

Saugerties Cottage with Creek Access

5–10 May

€ 132 per night
Superhost

Home in Woodstock

4.94 out of 5 average rating, 876 reviews

1822 Lewis Cottage - Sauna, Jacuzzi, Swimming Hole

9–16 Jun

€ 346 per night
Guest favourite

Cottage in Woodstock

4.95 out of 5 average rating, 187 reviews

Stunning Woodstock 1 BR Hideaway

23–30 May

€ 214 per night
Guest favourite

Guest house in Bearsville

4.98 out of 5 average rating, 463 reviews

Relax on the Ridge - 2 miles from Woodstock

24–31 Mar

€ 176 per night
Guest favourite

Cabin in Boiceville

4.98 out of 5 average rating, 434 reviews

Winston's Place - Woodland Cozy Catskills Cabin

14–21 Feb

€ 161 per night
Guest favourite

Guest house in Mount Tremper

4.97 out of 5 average rating, 298 reviews

Artful and Serene Woodstock Getaway

19–26 Sep

€ 124 per night
Superhost

Guest house in Saugerties

4.9 out of 5 average rating, 107 reviews

Fireside Cabin Retreat near Woodstock & Saugerties

22–29 Apr

€ 136 per night
Guest favourite

Cabin in Saugerties

4.98 out of 5 average rating, 158 reviews

Pine Rock House - A modern cabin getaway

7–14 Jul

€ 237 per night
Guest favourite

Guest house in Woodstock

5.0 out of 5 average rating, 292 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

22–29 Dec

€ 216 per night

Destinations to explore

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  4. Ulster County
  5. Woodstock
  6. Overlook Mountain