
Holiday rentals in Surprise
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Top-rated holiday rentals in Surprise
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Sweet Farm Stay
For an extra fee we also offer… ** FARM CAMP** May-Dec. Perfect for kids & families. 2 hours of farm chores, pony-riding, crafts every morning. Extra fee: $100/day. ** CRAFT RETREATS** All meals included. Wool/wood/kitchen craft. Work on the farm, MAKE stuff, and enjoy the outdoors. Extra fee: $250/person, min 5 people. **WRITING RETREATS** All meals included. A weekend of intensive writing + a break from internet. Extra fee: $250/person, min 5 people. Find us on ig—honeyhollowfarmstay!

Athens, NY House - 1 Bedroom "Want to Get Away"?
Athens, NY Entire House - 1 bedroom Quiet Country setting Winter time is a great time to escape to upstate NY. Guests have called it "a very cozy cottage in the woods". It is set back off the road and a great place to get away and unwind. 10 minutes from Exit 21 on the NYS Thruway and is an easy drive to several towns on the Hudson River. They are known for their restaurants, local shops and quaint downtowns. Area features outdoor activities: hiking trails, skiing,snowboarding and kayaking.

The Cabin - Ski House near Windham
The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Tiny Home A-Frame with Hot Tub & Creek
Just a little over 2 hours from NYC, the Cozy A-Frame is a 400 sq foot, eco-friendly, creekside cabin set in the Northern Catskills of New York. Our brand new home has been thoughtfully designed to include many indulging comforts while secluded in nature. Take in the calm of the woods from the hot tub or while roasting s'mores at the fire pit. Or turn up the music on the vintage stereo and watch the snow fall. An ideal getaway for those seeking a romantic escape or a change of pace to WFH.

Blacksmith House - Charming Historic Getaway
Built in 1790 as a blacksmith shop named “The Town Ax," Blacksmith House was rebuilt in the early 1990's and renovated by the present owners in 2017. The roughhewn beams of the original structure are exposed in every room. Approached by a grand stone staircase, set in a lilac-lined hamlet with plantings, surrounded by wildflowers, furnished with antiques and primitive Americana, Blacksmith House radiates tranquility and graciousness with its full-width front porch and classic proportions.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Luxury Hot Tub Ski Farmhouse Retreat on 50 acres
Just two hours from NYC, on 50 acres in the Catskill Mountains, this sun-drenched home was renovated by a luxury hotel designer in 2021. Each bedroom has a full en-suite bathroom, while common spaces are large and abundant, making this a perfect place for groups. Large brand new kitchen and dining, dedicated office space, game room, outdoor fire pit, cedar wood hot tub, outdoor shower. 12 MIN: Windham 25 MIN: Hudson 10 MIN: Grocery/Pharmacy 5 MIN: Zoom Flume Waterpark

Mountain View Retreat~Sunny Hill Golf / Skiing
Welcome to Sunny Hill Road ! We are located in a small community of private homes in an open space overlooking the mountains. This one bedroom unit has everything you need to enjoy your stay in the Catskills. Relax on the private deck or inside with amazing views from every window. The kitchen is fully equipped and ready to cook a full meal and then enjoy it in the dining room overlooking the mountains. It is quiet and restful here, amazingly beautiful in all four seasons!

The Orchard at Hover Farms
Come escape to the beautiful Hudson Valley countryside at The Orchard at Hover Farms. Take in views of both the Catskill and Berkshire mountain ranges from atop our rolling pastures. Our beautiful 1880 farmhouse will make you feel right at home with her authentic charm and calming atmosphere. This is a working farm where you can enjoy the sights and sounds of cattle grazing. During colder months enjoy the area's best ski resorts, most within 35 miles of the farm.

Contemporary Cabin in Catskill Mountains
Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Magic Forest Farm's Mountain View Suite
Our 225 acre farm is predominantly forested, with miles of hiking trails and incredible views. Nestled in the foothills of the Catskills near Albany, we are the last home on a dead end road and have multiple secluded rentals. We are a homestead devoted to the principles of organic farming and self reliance. We grow much of our own food and forge many types of wild mushrooms. You will be sure to enjoy friendly animals around the farm and a private fenced Koi pond.

Cozy Cottage By The Farm
Rest and relax at our newly renovated and peaceful cottage overlooking the beautiful Vertical Limits Horse Stables. We are conveniently located 5 mins from thruway North and South, HITS horse show, restaurants, shopping and everything else that Saugerties has to offer. A scenic 10 min drive will take you to Kingston or Woodstock, and approx. 30 mins away from Windham and Hunter Mountain Ski resorts.
Popular amenities for Surprise holiday rentals
Other great holiday rentals in Surprise

5-BR Villa with Pool and Dog Friendly!

Charming Hudson Farmhouse

Secluded Chalet in the Northern Catskill Mountains

Waterfront Lodge - Private Lake

Mountain View Condo • Windham

Gorgeous Modern New Ranch near Rail Trail!

Catskills Cabin -Wood Stove, Games, Coffee & Views

Amazing Woodstock escape
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Hunter Mountain
- Belleayre Mountain Ski Center
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Saratoga Spa State Park
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- National Museum of Racing and Hall of Fame
- June Farms
- Hancock Shaker Village




