Town of Pine Plains, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Pine Plains, New York on RentalSaver.com!

Town of Pine Plains Rentals

From $1131 per night (USD)
VRBO
Secluded and Spectacular Views
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
The Silo Set on 700 acres of wooded Hudson Valley real estate, The Silo is reached by crossing a bridge over a flowing ...
From $1131 per night (USD)
VRBO
From $612 per night (USD)
Expedia
Mid-Century Home Surrounded by Meadows
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Hideaway This mid-century modern home reigns over a magical world in the heart of New York State’s historic Hudson ...
From $612 per night (USD)
Expedia
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VRBO
Lakefront property at its finest. Nearby fantastic skiing slopes.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Lakefront property at its finest, recently renovated designer house. Beautiful Twin Island Lake. The peace and tranquill ...
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VRBO
From $386 per night (USD)
Expedia
Twin Island Lake House • Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with p ...
From $386 per night (USD)
Expedia
From $730 per night (USD)
VRBO
This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
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 ...
From $730 per night (USD)
VRBO
From $526 per night (USD)
Expedia
Lakeside Peninsula Escape
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Wake up to stunning views at this lakefront guest house on a private peninsula in Pine Plains, New York. Enjoy the lake ...
From $526 per night (USD)
Expedia
From $651 per night (USD)
VRBO
Willow Vale • Stunningly Designed Historical Icon w/ Hot Tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to our historic & meticulously restored home, Willow Vale, situated on a quiet & idyllic country road and nestle ...
From $651 per night (USD)
VRBO
From $298 per night (USD)
VRBO
Rustic 2 bedroom Stissing Lake Guest Cabin
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to Stissing Lake Guest Cottage, a newly renovated 2-bed, 2-bath retreat in the Hudson Valley. Nestled on an 11-ac ...
From $298 per night (USD)
VRBO
From $623 per night (USD)
VRBO
The Grey House + Loft Apt @ The Library Retreat
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Summary: Discover The Grey House & The Blue House at The Library Retreat, a renovated mid-century guest house and separa ...
From $623 per night (USD)
VRBO
From $635 per night (USD)
Expedia
The Red House @ The Library Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Discover The Red House at The Library Retreat, a captivating mid-century farmhouse in Pine Plains, just 2 hours ...
From $635 per night (USD)
Expedia
From $508 per night (USD)
VRBO
The Cabin-A quiet get away for rest and relaxation
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Quiet escape from the world. The Cabin settles into its surroundings with deceptive subtlety, while inside it is surpris ...
From $508 per night (USD)
VRBO
From $272 per night (USD)
VRBO
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Rustic cabin by Twin Island Lake, Pine Plains, NY Sitting on quiet Lake Road and nestled in the woods, my rental built i ...
From $272 per night (USD)
VRBO
From $1791 per night (USD)
VRBO
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
Bedrooms:
9
Bathrooms:
9
Sleeps:
22
The Pines includes a gourmet eat-in kitchen, butler's pantry, formal dining room, music room, library/game room, mud roo ...
From $1791 per night (USD)
VRBO
From $1402 per night (USD)
VRBO
Stissing Lake House | Hudson Valley Lake Front
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Picture yourself lying in the hammock or with a glass of wine on the porch. Jump into the lake for a refreshing swim, or ...
From $1402 per night (USD)
VRBO
From $1054 per night (USD)
VRBO
A Country Lodge Straight Out of the Pages of a Great Novel
Bedrooms:
0
Bathrooms:
4
Sleeps:
12
The Lodge Imagine a country lodge straight out of the pages of a great novel. Rustic chic combines with modern ameniti ...
From $1054 per night (USD)
VRBO
From $232 per night (USD)
Expedia
Adorable secret hideaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
The Nook (Silo garage apartment) This adorable secret hideaway is a self-contained efficiency apartment set in the mids ...
From $232 per night (USD)
Expedia
From $1055 per night (USD)
VRBO
Upstate Mountain View Retreat
Bedrooms:
5
Bathrooms:
6
Sleeps:
11
Escape to this stunning mountain retreat in Dutchess County. This spacious home comfortably accommodates up to 10 guest ...
From $1055 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Historic Cottage w Brand New Hot Tub and Game Room
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Restored 1810 cottage where historic charm meets modern living. Follow and tag us on IG @theupstatecub! Welcom ...
From $388 per night (USD)
Expedia
From $493 per night (USD)
VRBO
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Renovated & charming 3BR, 2BA home with spacious yard situated across from Mashomack Polo fields in the picturesque Huds ...
From $493 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Country Chic Lake House in Pine Plains
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Country Chic home in the beautiful Hudson Valley. 2.5 hour drive from NYC and Long Island. Historical town of Pine Plai ...
From $311 per night (USD)
Expedia
From $190 per night (USD)
VRBO
Stylish Pine Plains Home Near Parks & Hiking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Small town charm meets modern convenience at this updated home in Pine Plains! With 1 bedroom, 1 bathroom, and a fully e ...
From $190 per night (USD)
VRBO
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VRBO
Off Market
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Off Market !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! ...
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VRBO
From $443 per night (USD)
VRBO
Tanner Farmhouse - Rural Cozy Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Experience the charm of Tanner Farmhouse, a rustic yet modern home in Pine Plains, NY. This meticulously renova ...
From $443 per night (USD)
VRBO
From $1556 per night (USD)
VRBO
The Library Retreat: 3 Building Estate w/Pool+Pond
Bedrooms:
5
Bathrooms:
7
Sleeps:
12
Summary: Discover "The Library Retreat," a captivating multi-farmhouse in Pine Plains, just 2 hours from NYC. Set on a v ...
From $1556 per night (USD)
VRBO
From $1036 per night (USD)
VRBO
Post & Beam • Stunningly Designed Luxury Home w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the immaculate and professionally-designed post & beam rental home of two New York creatives, including the F ...
From $1036 per night (USD)
VRBO
From $932 per night (USD)
Expedia
The George is an elegant restored home in the Hudson Valley
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The George is a beautiful perfectly restored turn of the century home in the heart of Hudson Valley horse country. On a ...
From $932 per night (USD)
Expedia
From $905 per night (USD)
VRBO
Enchanting cottage in a private oasis
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Newly renovated cottage located at Ingadi Farmhouse, a family owned and run farm situated on 127 acres of land in the Hu ...
From $905 per night (USD)
VRBO
From $444 per night (USD)
VRBO
The Blue House - St. Peter Hill Summit
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
3 Bedroom modern house including 2.5 Bathrooms with open living space. This house impresses with its warm, modern an ...
From $444 per night (USD)
VRBO
From $3302 per night (USD)
VRBO
The Entire Estate at Picardy Farms
Bedrooms:
7
Bathrooms:
10
Sleeps:
20
Enjoy complete privacy across this 10-acre estate, perfect for retreats, large gatherings, or peaceful escapes. You'll ...
From $3302 per night (USD)
VRBO
From $464 per night (USD)
VRBO
Hudson Valley - Picardy Farm: The Barn
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The bright and cozy Barn has just been renovated and is part of the Picardy Farm, surrounded by an idyllic pastoral set ...
From $464 per night (USD)
VRBO
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VRBO
Hudson Valley - Picardy Farm: The Garden House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This impressive Bright and Sunny 3 Bedroom and 2.5 bath home is comfortable and quiet. With 2 queen bedrooms, 2 single b ...
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VRBO
From $816 per night (USD)
VRBO
1990s Cape Cod in Upstate NY
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This is a Cape Cod style home built in 1994. Recently under new ownership and not fully furnished, as we are about to u ...
From $816 per night (USD)
VRBO
$PLAYGROUND IN PARADISE!\n4BR w TENNIS, PICKLEBALL, POOL, NEAR MANY WEDDING SITES$
From $1034 per night (USD)
VRBO
PLAYGROUND IN PARADISE!\n4BR w TENNIS, PICKLEBALL, POOL, NEAR MANY WEDDING SITES
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
A bucolic retreat, this completely secluded estate, nestled on over 50 acres, offering your exclusive use of on site ac ...
From $1034 per night (USD)
VRBO
From $3441 per night (USD)
VRBO
The Farm House w. Garden Cottage at Picardy Farms
Bedrooms:
6
Bathrooms:
7
Sleeps:
8
Welcome to The Farm House, a spacious 1830 Greek Revival landmark residence at Picardy Farms. This lovingly restored 1 ...
From $3441 per night (USD)
VRBO
From $181 per night (USD)
VRBO
the suite @ barn & bike - private, bucolic, serene setting
Bedrooms:
0
Bathrooms:
1
Sleeps:
2
A 675 sq ft. fully private suite with your own entrance in an early American eyebrow colonial. The well appointed space ...
From $181 per night (USD)
VRBO
From $363 per night (USD)
Expedia
rural, serene + sophisticated space
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
In the country, yet short drives to the Hudson River Valley's towns. So many guests have a hard time leaving to go out ...
From $363 per night (USD)
Expedia

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Town of Pine Plains Rentals

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Results: 36 Rentals