Holiday houses in Pine Plains

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Top-rated holiday rentals in Pine Plains

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Guest favourite

Cottage in Pine Plains

5.0 out of 5 average rating, 132 reviews

Patchin Mills Quaint Country Cottage

Welcome to your cozy cottage in the bucolic Hudson Valley. Only 90 mi. north of NYC. We welcome small dogs, under 25 lbs. with prior host approval. Sorry, NO CATS. Enjoy biking, hiking, skiing, local culture or just relaxing. 1 mile outside a charming village in farm and horse country, your cottage has a full kitchen/LR, 2 BRS (1 queen, 1 full), bathrm, washer/dryer, deck, patio & yard. Close to colleges, dining & activities. We hope that you will love this corner of the world as much as we do.

5–12 Jan

$334 NZD per night

Guest favourite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

14–21 Oct

$207 NZD per night

Guest favourite

Apartment in Red Hook

4.85 out of 5 average rating, 192 reviews

A&A's Upper Red Hook

This comfortable, light-filled apartment is located under 10 minutes from Bard College, Fisher Center and Red Hook Village. Private entrance leads to the space that includes the full-size bed (not queen) and a sofa/futon for additional guests. The ensuite bath features a lovely tiled shower. A kitchenette includes large air fryer, microwave. The dining/work space is a mahogany table. Mesh WiFi. Roku TV. Air conditioning, off street parking round out the features. An easy choice for your visit.

18–25 Jun

$228 NZD per night

Superhost

Cabin in Rhinebeck

4.89 out of 5 average rating, 166 reviews

Immaculate, Secluded Cabin with Pond Close to Town

Newly renovated cottage on 14 acres with private pond and expansive lawn. The house has been furnished in beautiful, mid-century style with high end appliances and comfy gathering spaces. With abundant windows for enjoying the natural light and serene surroundings, this home feels entirely private but is 6 minutes from the quaint village of Rhinebeck, with all its adorable shopping and everyday staples. Nearby attractions include Bard College, The Omega Institute, Dutchess County Fair Grounds.

18–25 Sep

$693 NZD per night

Guest favourite

Guest suite in Red Hook

4.89 out of 5 average rating, 294 reviews

the farmhouse suite at gallatin farmstead

A 575 sq ft. fully private suite with your own entrance in a beautiful early American eyebrow colonial. The mid-century farmhouse style is highlighted by a darling kitchenette. And don't forget the bathroom hot steam shower! Of note, with a 30$ fee, we can set up a 2nd bed in the suite living room. We're happy to do it, it just takes some time to get together. It's a super comfortable mattress, the same model as the queen bed. We are also cycling happy and offer bike rentals and tours.

16–23 Nov

$281 NZD per night

Guest favourite

Cabin in Pine Plains

4.98 out of 5 average rating, 173 reviews

The Upstate A - Modern Luxury in the Hudson Valley

The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

4–11 Aug

$1,339 NZD per night

Guest favourite

Cottage in Pine Plains

4.98 out of 5 average rating, 118 reviews

Pine Plains Cottage

Located just 2 hours north of NYC, our country cottage in bucolic Pine Plains is newly renovated and furnished in a modern yet cozy style, welcoming you to a relaxing retreat! It is located in the heart of Pine Plains, a short walk to the town center. Perfect for 2-4 people. We currently have a 2 night min. stay and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your pet or a shorter stay!

23–30 May

$271 NZD per night

Guest favourite

Home in Pine Plains

4.98 out of 5 average rating, 110 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

23–30 Nov

$645 NZD per night

Guest favourite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door.

8–15 Dec

$280 NZD per night

Guest favourite

Apartment in Stanfordville

4.95 out of 5 average rating, 152 reviews

Country Apartment great for a romantic getaway

Second story apartment above garage with private entrance has everything you need for a comfortable getaway. Located on quiet rural neighborhood road with off street parking. Enjoy nature right out your door walking to the beaver pond in the back woods or on the many nearby hiking and biking trails. Relax in the backyard. An easy drive from the Taconic Parkway or 20 minutes from the Metro-North Wassiac train station.

25 Jun – 2 Jul

$240 NZD per night

Guest favourite

Apartment in Millerton

4.8 out of 5 average rating, 230 reviews

Gardens Galore and Village Whimsy Retreat

My place is close to restaurants and dining, the city center, and parks. My place is good for couples, solo adventurers, business travelers, and families (with kids). It is a steal for the price. nothing is as good around here, a true bargin. The apartment is below the 1850's victorian house. During the day you can hear children's feet pitter patter. After 7 The place is quite.

18–25 Jan

$189 NZD per night

Guest favourite

Home in Millerton

4.96 out of 5 average rating, 112 reviews

Vacation Home In Millerton

This is a house to enjoy with the family with a lot of space and many activities, in a small town but with a lot of tourism. You can visit the town which it has a small cinema, and Rail trail for walking or biking, and it has many restaurants nearby. This house includes a living room, kitchen, 4 bedrooms, 3 full bathrooms, deck, and a big backyard. You can also do BBQ s outside.

5–12 Sep

$341 NZD per night