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Vacation rentals in Pine Plains

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Top-rated vacation rentals in Pine Plains

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Cottage in Pine Plains

5 out of 5 average rating, 140 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.

Rental unit in Copake Falls

4.92 out of 5 average rating, 299 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!

Rental unit in Pine Plains

4.98 out of 5 average rating, 145 reviews

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.

Guesthouse in Germantown

4.98 out of 5 average rating, 186 reviews

The Loft

This beautiful loft apartment is located in the heart of Germantown- just 0.3 miles from Otto's Market (groceries and deli), Gaskins Restaurant, "A charming eatery serving a locally-sourced menu of classic American fare in a rustic dining room." And Universal Cafe. " farm to table global inspired classics." We offer tea & coffee in the loft, parking, yard access, wifi, basic amenities, full kitchen and a smart TV that has a fire stick with access to Amazon Prime and Netflix (no cable).

Guest suite in Millerton

4.93 out of 5 average rating, 348 reviews

Romantic Sunset-50 mile view!

ROMANTIC LUXURY! Fall is beginning now. Lesves are starting to turn and the nights are crisp and cool. Fresh mountain air. Clear starry nights. Your own private suite, entrance, kitchen, bathroom, outdoor dining facilities, bar b q grill. Located atop a mountain with magnificent SUNSET view 50 miles overlooking the Hudson River Valley. Completely steam cleaned, disinfected and sterilized before each guest. HEPA Air filters installed. High speed WIFI, 500mbps! 55” 4K HD TV;

Guesthouse in Stanfordville

4.93 out of 5 average rating, 179 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Guest suite in Red Hook

4.91 out of 5 average rating, 334 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! Please note 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. We are also have a cycling side business offering bike rentals and tours.

Cabin in Pine Plains

4.98 out of 5 average rating, 196 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

Cottage in Pine Plains

4.98 out of 5 average rating, 130 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!

Home in Pine Plains

4.98 out of 5 average rating, 120 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.

Cottage in Rhinebeck

4.88 out of 5 average rating, 169 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we used a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Farm stay in Ancram

4.96 out of 5 average rating, 295 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. Just Added mini split AC!

Vacation rentals for every style

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Hotels

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Homes

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Popular amenities for Pine Plains vacation rentals

Free parking on premises

Air conditioning

Stay near Pine Plains's top sights

Stissing House45 locals recommend

Stissing Mountain Fire Tower Parking Area36 locals recommend

Peck's Food Market21 locals recommend

Hammertown Barn13 locals recommend

Lia's11 locals recommend

Tower Pizza11 locals recommend

Other great vacation rentals in Pine Plains

Home in Pine Plains

5 out of 5 average rating, 31 reviews

Stunningly Designed Luxury Home w/ Pool & Hot Tub

Home in Pine Plains

4.86 out of 5 average rating, 22 reviews

Historic Cottage w Brand New Hot Tub and Game Room

Farm stay in Red Hook

4.78 out of 5 average rating, 295 reviews

Farmland Tranquility at The Greig Farm Schoolhouse

Rental unit in Red Hook

4.96 out of 5 average rating, 23 reviews

Hummingbird apt

Home in Kingston

4.97 out of 5 average rating, 317 reviews

This New House

Home in Millerton

4.98 out of 5 average rating, 49 reviews

1800s Schoolhouse with Modern Amenities

Home in Ancramdale

4.97 out of 5 average rating, 72 reviews

Modern Farmhouse with Mountain Views on 28 Acres

Guesthouse in Millerton

4.98 out of 5 average rating, 92 reviews

Loft in the Pines

Quick stats about vacation rentals in Pine Plains

Total rentals
20 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

What are the most popular amenities for House Rentals in Pine Plains?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
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.
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.
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 family-friendly vacation rentals in Pine Plains?
Pine Plains has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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 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 wifi?
Absolutely! We offer over 10 house rentals with wifi in Pine Plains. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore