Holiday houses in Chester

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Top-rated holiday rentals in Chester

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Guest favourite

Cottage in Greenwood Lake

4.92 out of 5 average rating, 142 reviews

Cozy home in the Village of Greenwood Lake

Adorable country retreat under an hour from NYC - perfect for a romantic couples getaway or a family of 4. Located in the village, our quaint cottage is walkable to everything; Restaurants, bars, grocer, cvs, bagels, bus stop and even the public beach!! Minutes away from TONS of local attractions; drive-in, skiing, renaissance fair, wineries, shopping, lake activities, orchards, creameries, parks, Appalachian trail, spa, rafting, golf, water park, & so much more. Pets welcome! Permit #21-07603

Guest favourite

Guest suite in Montgomery

4.95 out of 5 average rating, 424 reviews

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

Guest favourite

Cabin in Vernon Valley

4.97 out of 5 average rating, 351 reviews

Serenity Cabin, the historic waterfall cabin!

Escape to a magical paradise where the sound of a babbling stream & chirping birds create a symphony of serenity. Nestled on 18 acres of pristine wilderness, this secluded retreat offers endless opportunities for exploration & adventure. Wander along the streams and discover hidden waterfalls, all while immersing yourself in the breathtaking beauty of nature. Located 5 minutes from Mountain Creek, Warwick drive-in, Appalachian trail, & activities like goat yoga, horse riding, & TreEscape adv.

Guest favourite

Guest suite in Chester

4.95 out of 5 average rating, 237 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, and has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, a French door shower, and a kitchenette with sunny breakfast nook. It is freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Guest favourite

Cottage in Monroe

5.0 out of 5 average rating, 129 reviews

Cozy Lake Cabin

Make wonderful memories on pristine Walton Lake. 1 hr from NYC . This ALL INCLUSIVE Waterfront Cabin is like a mini resort! Rustic, rugged, off grid feel yet 2 miles from town. It has 2 docks, over water hammock & fire pit🔥. Enjoy sunsets on the covered porch & deck. Fish, & look for bald eagles🦅 Hungry? Paddle🛶 across the lake for tacos🌮 & drinks🍸. Inside has abundant retro & antique decor, modern appliances, fireplace♨️, & strong WIFI. Includes Free Firewood, NO CLEANING/PET FEES🐕

Guest favourite

Cottage in Goshen

4.93 out of 5 average rating, 198 reviews

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.

Guest favourite

Apartment in Warwick

4.95 out of 5 average rating, 156 reviews

THE GEM: In The Heart Of It All!

Enjoy a COZY, CLEAN and NEWLY RENOVATED apartment with an OUTDOOR BALCONY, located in the heart of Warwick! All the great restaurants and shops within walking distance. SPECIAL PRICING FOR MONTH LONG STAYS DURING THE WINTER SEASON. This wonderful apartment comes with a fully equipped kitchen, queen bed, full bath and tub. This apartment has its own entrance and is very PRIVATE. FREE PARKING LOT within walking distance of apartment and WiFi enabled smart TV with a Netflix subscription.

Guest favourite

Apartment in Warwick

4.98 out of 5 average rating, 350 reviews

Warwick Village Apt w Off St Parking

2 minutes to Warwick Village Farmers Market Our lovely apartment has earned 5 star reviews from over 300 guests. You'll love this private suite w private entrance Large kitchen, bedroom & stunning sun room loaded with plants Loved by gardeners, bicyclists, runners, artists, writers, diners, & shoppers. Visit Brew Pubs & Wineries, Woodbury Common, West Point, Catskills, Mt Peter, Mountain Creek, Heated bathroom floor & large shower Beautiful gas stove 300 MBPS Washer & dryer

Guest favourite

Tiny home in New Paltz

4.99 out of 5 average rating, 745 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Guest favourite

Guest suite in Warwick

4.95 out of 5 average rating, 268 reviews

Suite on Longhouse Creek

Beautiful one bedroom private suite with comfy queen size bed. The suite includes a sitting room, overlooking the creek, full bath, coffee nook with small refrigerator, microwave and Keurig coffee maker. Coffee is provided. A spiral stair leads you to the private deck with a french door entrance. Enjoy your coffee sitting at the lovely bistro set overlooking the longhouse creek. Feel free to use yard seating by the creek. Town Permit # 32042

Guest favourite

Apartment in Chester

4.96 out of 5 average rating, 340 reviews

Luxury Apt/Sugar Loaf/10 Min To LEGOLAND

This lovely modern space was just built in 2015. The space is located in the quaint Hamlet of Sugar Loaf, New York Artisan Village, which is surrounded by the town of Warwick and Chester with Greenwood Lake just minutes away...and NYC is just 75 minutes. It's a second floor apartment with private front and back entrances. Rear deck overlooks spacious fenced in yard with pond view. Walking distance to 2 restaurants and deli. LEGOLAND just 8 miles!

Guest favourite

Home in Chester

4.98 out of 5 average rating, 121 reviews

The Little Green Farmhouse

Built in the mid 1800s, this 2,400 square foot farmhouse is a comfortable country getaway with space for the whole family. Nestled on 2.5 acres, the house is perfectly positioned between the villages of Warwick and Sugar Loaf. It has 4 bedrooms with the ability to sleep 8 people. There are also 2 full bathrooms, a dining room, living room, office space, fully equipped kitchen, and a bonus space with a table to play board games, cards or puzzles.