Holiday rentals in Town of Crawford

Charming Revitalized 1920s Country Style Home

Venture back in time in this tastefully appointed historical residence. First floor apartment is a quaint abode showcasing boutique furnishings and decor, contrasting textures and motifs, arched doorways, a covered front porch, and a walkout to the backyard. We are 20 minutes away from Legoland, also located near Wallkill, and an easy drive to Warwick and Patterson. Our home is eclectic and unique, placed in the historic district of pine bush. This home provides up to date appliances and cozy furnishings while still holding onto that good ol’ 1920’s feel. Plenty of room for dining in and an easy ride or walk to great food. This home is bright and cheery yet provides privacy and warmth. The entire first floor is your domain. With a private entrance and easy parking. The locked doors you will encounter is for your privacy. There are permanent renters above you, however they have their own entrance and are completely separate. Trust us you won’t need more space than what’s provided, very roomy with a closet in each room, as well as in the dining area. Up until your check in we are available to you through Airbnb with any questions or concerns you might have. After check in most vacationers prefer to hit the ground running and begin enjoying their stay, however for little bumps in the road a number will be provided in order to continue taking care of you. The property boasts easy access to hikes, Wallkill Farms, wineries, Legoland and is walking distance from multiple restaurants, antique shops, and more. We recommend renting a car. While this home is walking distance to restaurants and downtown pine bush the beautiful rural scenery means a little distance of 10-20 minutes of driving between wineries and hikes and other enjoyable activities. We want our guests to enjoy their time to the fullest, and know that we care about their stay. Which is why we like to make clear our home runs on city water. There is an initial aroma from the faucet, however it doesn’t last long and adjustments to that are in the process. We of course offer you filtered water for you and your family. This home is multiple stories which adds to its beautiful character. You and your family will be occupying the entire first floor. The upper level has permanent renters, however they have a separate entrance and are quiet, as well as accommodating.

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Little Yellow Cottage New Paltz - Kitchen wash/dry

Built over 100 years ago as a chicken hatchery, this gorgeous little gem has been fully restored as a two-story guest cottage. Located in New Paltz just minutes off Exit 18 on I-87 in a very private, quiet, country setting. Only ten minutes from New Paltz Village & SUNY New Paltz and set back on a lightly traveled road for those long summer strolls. You don't even need a car to get here! It's just 12 minutes by taxi from the New Paltz Bus Station or bring your bike up and cycle everywhere!

Sweet Cottage on a Farm Road

Simple, airy, studio cottage next to my house, featuring a woodstove & enormous bathroom with a clawfoot tub. Perfect for writers/solo-travelers seeking solitude & peace and couples wanting quality time together. The cottage is on a scenic country road, walking distance to 3 farms, including 2 great farm-to-table restaurants: Westwind Pizza/Apple Orchard, Arrowood Brewery, & Hollengold Farm. A stone's throw are Stonehill Barn and Inness. 15 min drive to the incomparable Minnewaska State Park.

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

Cheery & Peaceful Farm Cottage, 10 Min to LEGOLAND

When you're looking to get away from it all and experience some peace and quiet surrounded in nature, this Cottage fits the bill. Whether it's enjoying fireflies over the field at dusk or enjoying cheerful birds in the morning, this beautiful Cottage sets the stage for you to be refreshed and renewed by the time you check out. While it feels like a secluded oasis, this place is also 10 minutes from LEGOLAND, Target, and all your other favorite conveniences. We look forward to hosting you.

Modern BoHo 3BR Cottage Near by Hiking, Winery

Our newly modern bohemian cottage (aka Green House!) is perfect for your next weekend getaway or a new WFH locale. Decompress from city stress in this calm, serenely appointed private home. Close to attractions but far enough away to escape, you'll never want to leave. NYC: 79 mi. Hunter Mountain Ski Resort: 60 mi. Pine Bush - groceries/supplies: 7 mi. Middletown - shopping (Walmart, Target, Best Buy, Home Depot): 16 mi. Hiking trails: 7 mi. Horseback riding: 7 mi. Sky diving: 15 mi.

Just Around The Corner

This roomy, modern and immaculate apartment is situated conveniently near town, but far enough away that you can enjoy the countryside. Enjoy the view of the pond and sounds of nature. A one bedroom that sleeps six with three queen beds in separate rooms divided by doors. (Please note the listing price is for 4 guests. Each additional guest is $25 per night). We are 6 min to Middletown, 18 min to Legoland, 21 min to Wallkill, 49 min to Warwick and just under one hour to Patterson, NY.

Newly built apartment steps from Mohonk preserve.

Nestled amongst the trees below Bonticou Crag this is a great base camp for climbing, hiking and biking. Five minutes from New Paltz; I do recommend having a car to access the area. Shared yard and fire pit right outside. My family and I live in the main part of the house. The outside area and house are still under construction, I’m working on it but its not put together yet. The apartment and inside area are clean and newly built with their own mini split and air circulation.

Cozy Cottage | Sauna + Stone Patio w/ Firepit

Escape to a serene cottage nestled on the Shawangunk Ridge. Unwind by the fireplace, soak in the private infrared sauna (with direct patio access), or relax outside on the natural stone terrace with a firepit and forest views. Crafted with care—from a 100-year-old reclaimed wood dining table to a curated “meaningful library” and hidden messages—this space invites calm, curiosity, and connection. Near trails, lakes, and local adventure. Thoughtful, cozy, and quietly unforgettable.

Historic 1750s Farmhouse Apartment

Come explore the Hudson Valley from our newly renovated modern farmhouse apartment in a serene, bucolic setting. Located at the boundary of the towns of Gardiner and Shawangunk, beneath the beautiful Shawangunk ridge, there are plenty of adventures to be had! Hiking, biking, climbing, yoga class, and even sky diving are right here! And when you tire of all the outdoor fun, check out local wine, cider, and whiskey tastings, antiques shopping, and delicious local restaurants.