Holiday rentals in Orange County

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Top-rated holiday rentals in Orange County

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Guest favourite

Cottage in Greenwood Lake

4.92 out of 5 average rating, 139 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

6–13 Oct

€ 140 per night

Guest favourite

Cabin in Vernon Township

4.96 out of 5 average rating, 138 reviews

Mountain Creek Views Guest Suite

Guest suite/private side entry. Host lives upstairs. If you would like to have the host absent, there is a fee of $40 per night. Escape to our modern mountain retreat with breathtaking views and easy access to outdoor adventures - 2min to the Appalachian Trail - 8min to Mountain Creek - 10min to Warwick drive-in movie theatre - Hiking trails all over And when you're ready to relax, you'll have a comfortable and inviting space to call home. We take pride in providing exceptional hospitality.

2–9 Jan

€ 145 per night

Guest favourite

Guest suite in Montgomery

4.95 out of 5 average rating, 420 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

24 Nov – 1 Dec

€ 132 per night

Guest favourite

Guest suite in Chester

4.95 out of 5 average rating, 230 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.

31 Jan – 7 Feb

€ 110 per night

Superhost

Cabin in Greenwood Lake

4.88 out of 5 average rating, 161 reviews

Get some R&R at the Rustic Retreat!

The Rustic Retreat is centrally located, 2 bedroom 1 bath cozy cottage is just what you've been looking for in this lake community. There is a 3-6 car driveway, newly renovated kitchen, open floor plan in the dining & living room, new shed bar/ fire pit, & sleeps 7 (Q in Master, F Sofa Bed Couch, T Bunk Beds, F Air Mattress). Located about 3 mins from Greenwood Lake and 10 mins from Warwick, many activities for your perfect getaway! IG @Rusticretreat22 Short Term Rental Permit # 21-0422

17–24 Oct

€ 141 per night

Guest favourite

Cabin in Wurtsboro

4.98 out of 5 average rating, 203 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

29 Mar – 5 Apr

€ 306 per night

Guest favourite

Cottage in Newburgh

4.88 out of 5 average rating, 186 reviews

Cozy Lake Cottage

Cozy cottage in residential lake community, adjacent to historic fine dining restaurant. There is an approximate 150 yard walk down to the lake to enjoy the spectacular sunsets . Centrally located in the Hudson Valley near everything there is to experience. Located in our area Many Local Wineries ( Angry Orchard) Orange County Choppers Cafe Woodbury Commons Outlet Mall Historic Newburgh and Waterfront Culinary Institute of America US Military Academy New Paltz and Mohonk Mountain House

20–27 Jun

€ 135 per night

Guest favourite

Cottage in Goshen

4.94 out of 5 average rating, 194 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.

20–27 Mar

€ 146 per night

Guest favourite

Flat in Warwick

4.95 out of 5 average rating, 151 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.

12–19 Jul

€ 163 per night

Guest favourite

Guest suite in Warwick

4.95 out of 5 average rating, 267 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

31 Mar – 7 Apr

€ 147 per night

Guest favourite

Flat in Chester

4.96 out of 5 average rating, 333 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!

14–21 Apr

€ 173 per night

Guest favourite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

18–25 Apr

€ 82 per night