Holiday rentals in Surprise

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Top-rated holiday rentals in Surprise

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

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Top guest favourite
A spacious living area displays a mix of seating options, including a blue couch and two accent chairs. Natural light filters through large windows, highlighting the wooden beams above. A wooden table sits in the foreground, with a ladder leading to the loft visible in the background.
Flat in Earlton
4.94 out of 5 average rating, 310 reviews

Sweet Farm Stay

For an extra fee we also offer… ** FARM CAMP** Apr-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!

Top guest favourite
The exterior of a blue cottage is shown, set in a wooded area. A gravel driveway leads to the entrance, which features a wooden deck with steps. Lush greenery surrounds the structure, providing a serene atmosphere, while a small porch light and potted plants add subtle charm.
Home in Catskill
4.99 out of 5 average rating, 223 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

Athens, NY Entire House - 1 bedroom Quiet Country Setting Now is a great time to escape to beautiful 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. The area features outdoor nature activities: hiking trails, boating and kayaking.

Top guest favourite
A gravel road winds through a dense, green forest, leading toward a wooden cabin nestled among tall trees. Direct sunlight filters through the leaves, casting dappled patterns on the ground. The serene surroundings create a sense of seclusion and tranquility.
Cabin in Catskill
4.96 out of 5 average rating, 54 reviews

Romantic Getaway

Come stay at this sun-filled cabin in the Catskills ! This home away from home is all new construction and it contains all of the amenities you'll need to stay for just a weekend or for a whole week. The cabin is nestled in the woods, but it's centrally located near the town of Catskill, so you can have easy access to our popular ski mountains, our world renowned art scene and countless award winning nearby food destinations. Rich history of 17th century architecture, music and art await you.

Top guest favourite
An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.
Cabin in Saugerties
4.97 out of 5 average rating, 157 reviews

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

Top guest favourite
The cabin features a charming exterior with a blue-gray wooden facade and a bright red door. Large windows provide natural light to the space. Two red Adirondack chairs are positioned on the stone patio, inviting guests to relax in the natural surroundings.
Cabin in Climax
4.95 out of 5 average rating, 78 reviews

Catskills Cabin on 100 Wooded Acres, Private Lake

Relax and refresh in this unique, newly renovated cabin on 100 wooded acres! Located minutes from the town of Coxsackie, the Hudson River and the Catskill Mountains, this historic cabin blends rustic charm and access to nature with comfort and convenience. High-speed WiFi and a fully stocked kitchen make this a perfect remote work destination. Ready to explore? Hike 3+ miles of on-site trails, swim or canoe in the lake, tour nearby breweries, orchards and antique stores or kayak the Hudson!

Top guest favourite
A serene outdoor scene captures four individuals seated in Adirondack chairs facing a vibrant sunset over the Hudson River. The expansive lawn features gentle rolling hills and a backdrop of trees, enhancing the peaceful ambiance of the setting.
Guest suite in Hudson
4.99 out of 5 average rating, 124 reviews

Welcome to Casa Bartolo, Your Oasis on the Hudson!

It's now Lilac season! Why book a hotel when you can enjoy a charming, private 2-bedroom suite with breathtaking views of the Catskill Mountains, Hudson River, and stunning sunset! This tranquil retreat offers: Private Entrance, Private shared Bathroom, Kitchenette, cedar soaking tub & easy parking. Wake up to the sunrise and enjoy a cup of Nespresso or tea. Whether you want to relax, walk, jog, bike, meditate, smell the lilacs & pick eggs or simply unwind, this is the perfect escape.

Top guest favourite
A covered patio area is shown, featuring a wooden floor and two chairs next to a small table. The space is surrounded by screens, offering views of the grassy lawn and the Hudson River in the distance, with trees framing the scene.
Flat in Coxsackie
4.99 out of 5 average rating, 155 reviews

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Top guest favourite
A modern bungalow is illuminated at dusk, featuring large glass doors that reveal a warm interior. A spacious deck area is adorned with string lights and includes comfortable seating options, inviting relaxation amid the surrounding trees.
Bungalow in Cairo
4.99 out of 5 average rating, 542 reviews

Modern Riverfront, Swim & Fish, 20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Superhost
Home in East Jewett
5 out of 5 average rating, 3 reviews

Creekside Couple's Escape w/ Hot Tub Sauna & More!

Nestled beside a charming creek, our newly renovated cabin offers a peaceful escape where nature and comfort come together. Relax with your partner in the hot tub, on the covered deck, unwind in the wood-fired sauna, or sit by the fire in the gazebo. Enjoy the calming sounds of the creek and the outdoor views from every window. Discover nearby trails, quaint towns, lakes and waterfalls. Pet-friendly and ideal for couples looking for a unique getaway any time of year.

Top guest favourite
A modern cabin exterior is set against a backdrop of colorful autumn foliage. The structure features large glass doors and windows, allowing natural light to flow inside. A spacious lawn is visible, complemented by seating arrangements on the patio, inviting relaxation in nature.
Cabin in Round Top
4.99 out of 5 average rating, 160 reviews

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.

Guest favourite
A rustic cabin is nestled within a lush landscape, surrounded by vibrant greenery and wildflowers. Adjacent to the cabin, a shaded cooking area is visible, with smoke gently rising from a fire pit, set against a backdrop of rolling hills and trees.
Tiny home in Roxbury
4.97 out of 5 average rating, 211 reviews

Birdhouse: A Starry Escape in the Catskills

The Birdhouse at Bellfire in Catskills located on a bucolic property in the Catskills Mountains surrounded by maple forest, wildflowers field, and miles to roam. The cabin features a 6 ft skylight above the bedroom, an ode to the awe-inspiring skies of the Meeker Hollow, one of the best spots for stargazing in NY state, and an 11ft-tall window wall in the living space, framing the sprawling, lush landscape. Off-grid & unplugged—see full details before you book.

Guest favourite
A hot tub is positioned on a wooden deck, inviting relaxation. A single chair sits nearby, offering a view of a lush landscape featuring trees with autumn foliage. Clear blue skies enhance the serene outdoor setting.
Cabin in Catskill
4.91 out of 5 average rating, 197 reviews

Cabin Oasis near Town

Greetings and welcome to our delightful, recently remodeled cabin, seamlessly combining modern coziness with the allure of rustic charm. Situated within a welcoming Catskills neighborhood, this snug haven ensures an authentically comfortable escape. Step through the door to uncover a welcoming, well-planned interior that caters to your home-like needs. Savor your morning coffee on the deck or indulge in a soak in your exclusive hot tub.

Popular amenities for Surprise holiday rentals

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Surprise