
Holiday houses in Pine Plains
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Top-rated holiday rentals in Pine Plains
Guests agree: these stays are highly rated for location, cleanliness and more.

Slate Cabin - Stylish Country Escape x Rhinebeck
This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

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.

Design-Forward Riverfront Cabin on 120 Acres
Far from the road, a tranquil modern cabin sits directly above a state-stocked fly-fishing and tubing river - an intimate, private escape under two hours from NYC. Set on a 120-acre property, with access to trails, river swimming, and a private cabin beach, you’ll feel completely secluded while still being 10–30 minutes from Red Hook, Rhinebeck, Hudson, and Kingston. Radiant floors, a Swedish composting toilet, Tesla Powered, w/ 500 Mbps fiber internet make it easy to unplug without sacrificing.

Tanner Farmhouse - Rural Cozy Escape
Experience the charm of Tanner Farmhouse, a rustic yet modern home in Pine Plains, NY. This meticulously renovated 3 bed/2 bath home preserves history while offering modern comforts. Enjoy the living room's marble fireplace and chef's kitchen. Upstairs, 3 bedrooms provide comfort and a renovated bathroom with valley views. Outdoor spaces include a front porch, backyard patio & firepit with stunning vistas. This home combines history and luxury in a tranquil retreat in the heart of Pine Plains.

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Magical Private Island Retreat in Pine Plains
Enjoy the serenity of Twin Island Lake, surrounded by tranquil water, lush mountains and nature. this incredible private island retreat is only 2 hours from NYC. Take a canoe across a lily pad dotted lake to your own private island paradise. You will never find a magical space like this so close! The entire island is yours to enjoy and has plenty of outdoor spaces including a propane grill, hammocks and plenty of seating areas. The inside a humble aesthetic with wood paneling and charm.

Newly renovated cutie
Newly renovated apartment in private home. Pets may be allowed on a case by case basis. Please contact me to discuss. Ample parking off road. Quiet location. Centrally located. Hudson to the north (20 mins). Millerton (10 mins) to the East. Rhinebeck (20 mins)to the west. Poughkeepsie to the south. Summertime polo matches only 5 mins from the house. Town beach a couple mins away. Many dining options within minutes. The Stissing Center offering musical and theater options also within minutes.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

Stunningly Designed Historical Icon w/ Hot Tub
Welcome to our historic & meticulously restored home, Willow Vale, situated on a quiet & idyllic country road and nestled on 700' of Shekomeko riverbank. Built in 1790, the home was once the iconic "Mon Blason" - an inn and the *first French haute cuisine restaurant* in the Hudson Valley, owned and operated by Charles Virion, the former private chef to Orson Wells, Richard Rogers (of Rogers and Hammerstein), and John and Mable Ringling (of Ringling Bros and Barnum & Bailey Circus).

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 and fully renovated in 2020–2021, the home blends cozy cabin character with modern comforts for a relaxed yet elevated stay immersed in nature. You'll find great hiking in the summer, vibrant fall foliage, peaceful snowy winters, fresh upstate air year-round, and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

the farmhouse suite @barn & bike
A 620 sq ft. fully private suite with own entrance. The early American farmhouse is highlighted by a darling kitchenette, hot steam shower and original MCM furniture. We live on the other side of the eyebrow colonial, originally built in 1800. Please see the other details to note, including that the kitchenette has an induction stove top and convection air fryer toaster oven. It's a great for light cooking. Please ask for a grill for cooking meat and greasy food. Thank you!
Popular amenities for Pine Plains holiday rentals
Other great holiday rentals in Pine Plains

Cabin in the woods w/ sauna next to Lake Taghkanic

Family-Friendly by Polo + EV Chgr

Hudson Valley Farmhouse on a Country Lane

The Gallatin Farmhouse

Stony Hill Haus in Pine Plains

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

2bed farm stay as seen in Dezeen, architects cabin

Mtn Views | Fire pit |near Stissing House
When is the best time to visit Pine Plains?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $376 NZD | $331 NZD | $314 NZD | $362 NZD | $458 NZD | $462 NZD | $472 NZD | $483 NZD | $483 NZD | $504 NZD | $481 NZD | $472 NZD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Pine Plains?
Pine Plains has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Pine Plains?
Experience the best of Pine Plains with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Pine Plains?
Four-legged friends are welcome in Pine Plains. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Pine Plains?
Yes! Work meets play with ease at over 10 vacation rentals in Pine Plains featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Pine Plains have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Pine Plains. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pine Plains have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Pine Plains. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pine Plains have wifi?
Absolutely! We offer over 10 house rentals with wifi in Pine Plains. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pine Plains have free parking?
Absolutely! We offer over 10 house rentals with free parking in Pine Plains. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Pine Plains

Total holiday rentals
Explore 30 holiday rentals in Pine Plains

Nightly prices starting at
Pine Plains holiday rentals start at $192 NZD per night before taxes and fees

Verified guest reviews
Over 1,760 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Pine Plains holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pine Plains rentals

4.9 Average rating
Pine Plains stays are highly rated by guests—averaging 4.9 out of 5!
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