Vacation rentals in Overlook Mountain

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Top-rated vacation rentals in Overlook Mountain

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Guest favorite

Guesthouse in Bearsville

4.98 out of 5 average rating, 565 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.

Dec 14 – 21

R3,243 ZAR per night

Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 640 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.

Jan 22 – 29

R2,544 ZAR per night

Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 144 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Our cozy little cottage is tucked away adjacent to the woods. This single floor 650sf apartment is a perfect place to unwind, build a bonfire, & enjoy the nature that surrounds you. Wake up in the morning to watch deer while enjoying your coffee on the porch. Main St. Tannersville is only an 8 min walk; with its nice selection of restaurants & shops. Hunter Mountain & Kaaterskill Falls are within a 10 min drive . Woodstock, Saugertise, Windham, Catskill & Kingston are within a 35 min drive.

Jun 12 – 19

R2,588 ZAR per night

Guest favorite

Apartment in Woodstock

4.89 out of 5 average rating, 302 reviews

Hotel Woodstock - Tiger Lily Suite

Overlooking the Woodstock village center, this antique hotel has 148 years of history and charm. From the front steps you will feel the same energy that travelers have felt since President Ulysses S. Grant visited Woodstock in 1872. This room 3B is a 1 bedroom apartment with a separate living room with a queen sized sofa bed. There is a full kitchen and a private bath. You do not need a car! The Trailways bus from NYC stops directly across the green, and walk to everything in the village.

Sep 8 – 15

R2,301 ZAR per night

Guest favorite

Guesthouse in Woodstock

4.95 out of 5 average rating, 301 reviews

Pick Herbs at a Quirky Stone Cottage with BBQ and Fireplace

Snuggle by a roaring fire. Eat in a corner nook or at a rustic wooden counter by a window. This quaint, whimsical home has a private deck w/bbq, a garden with a hammock and fire pit. A full size Murphy bed with a full kitchen (except for an oven). You will have access to the entire guest house. A short drive to the beautiful, eclectic, funky town of Woodstock. Art & culture, restaurants, hiking & biking all nearby. Electric heat, ceiling fan, a standing ac unit and single person shower.

Nov 24 – Dec 1

R3,056 ZAR per night

Guest favorite

Guesthouse in Woodstock

4.86 out of 5 average rating, 831 reviews

Rocket Room - Rock Stars Only

Walk to town, hiking or a swimming hole. A popular vintage look cabin that backs up to a private woods but is steps from all Woodstock has to offer. Long time superhosts. Turn on, Tune in, Drop out in our 70's rock & roll hideaway carved out of a converted 1920s carriage house. This ain't your Grandma's cabin. All our units have been featured in videos, films, and photoshoots. This one has been featured in Playboy and Imperial Publishing arthouse book. Town of Woodstock OP #27.54-1-12

Apr 22 – 29

R2,433 ZAR per night

Guest favorite

Cabin in Saugerties

4.95 out of 5 average rating, 165 reviews

Cozy Cottage for Two

Unplug in this cozy cabin for two located in the scenic Hudson Valley. This intimate cabin is less than a two hour drive from Manhattan, and in the heart of many hiking trails and ski resorts. Set at the end of a private road, this cabin is furnished with a fireplace and all guests are welcome to use! When looking for a bite to eat, the historic village of Saugerties or vibrant village of Woodstock is just a quick ride away. Pets are welcome with an additional $40 cleaning fee.

Mar 29 – Apr 5

R2,976 ZAR per night

Guest favorite

Townhouse in Saugerties

4.92 out of 5 average rating, 288 reviews

15 min to Woodstock/Saugerties/Hunter (2 bedroom)

Private 2 bedroom home on a wooded lot. Owner lives on site. I live on one side, the other is your unit. Fully stocked kitchen, bathroom and on site parking. All linens and towels provided. 10 minutes from Woodstock & Saugerties. 100 miles from NYC. Located in the Catskills Private yard with fire-pit and BBQ. If you are looking for a weekend away to enjoy the quiet of the outdoors and close to great restaurants, hiking and swimming holes, this is the place.

Aug 6 – 13

R2,518 ZAR per night

Guest favorite

Cottage in Saugerties

4.93 out of 5 average rating, 216 reviews

Chic & Cozy Cottage 10 mins to Woodstock

Located on a bucolic country road on the border between Saugerties and Woodstock, this newly renovated 500 sq ft cottage is on a private acre filled with spaces to relax: screened in dining shed, fire pit, BBQ grill, a creek, forest & the magical sound of a hidden waterfall across the road. Just 10 min from Woodstock town square, 8 min to Levon Helm Studios, and 15 from Bearsville Theater, it's the perfect escape. (Pets welcome on a case by case basis. Please ask.)

Feb 21 – 28

R2,592 ZAR per night

Guest favorite

Barn in Woodstock

4.84 out of 5 average rating, 166 reviews

The Woodstock Barn Studio

Once a Woodstock chicken barn, your space is the lower level,of a renovated studio apt. that maintains its rustic charm with wide plank pine floors & ceiling beams. Only 2 blocks to down town Woodstock & bus stop to NYC . There are hiking trails for you to enjoy, the beautiful Wilson State Park as well as The stunning views of Cooper Lake, the Ashokan Reservoir & Rail Trail that will help sooth your spirit. Bring your camera! Well behaved pets welcome.

Jul 12 – 19

R2,393 ZAR per night

Guest favorite

Tiny home in Saugerties

4.94 out of 5 average rating, 218 reviews

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! “The Haven” at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

Apr 5 – 12

R2,364 ZAR per night

Guest favorite

Cabin in Woodstock

4.93 out of 5 average rating, 616 reviews

Byrdcliffe Artist Studio (27.1-1-70)

Historic Byrdcliffe Artist's Studio ... is a classic cabin in the woods where theater companies were launched, cartoon characters drawn, and famous books written. Quiet & inspirational, perfect for artists, couples, close friends, and small families. A place to breathe fresh air & see the stars. Everyone is welcome!

Jan 9 – 16

R4,049 ZAR per night