Pine Plains holiday rentals

We found 881 holiday rentals — enter your dates for availability
Discover a selection of 23 homes and other holiday rentals in Pine Plains that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a TV. You'll be sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Pine Plains

Showing deals for:8 Jan - 15 Jan

Private kitchen
Interior
Property grounds
Interior
Exceptional
(11 reviews)

Farmette Roquette Hudson Valley

Germantown

8% off
AU$7,535
for 7 nights, 1 room
AU$1,076 per night
includes taxes & fees
Farmette Roquette Hudson Valley
LIVING ROOM WITH DOUBLE SIDED FIREPLACE
Chefs Kitchen
EXTRA LONG COVERED PORCH W/ LOTS OF SEATING, OVERHEAD CEILING FANS & LIGHTING
Front door entry way
Exceptional
(38 reviews)

Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!

Ulster Park

6% off
AU$15,760
for 7 nights, 1 home
AU$2,251 per night
includes taxes & fees
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!
Living area
Interior
Private kitchen
Great Room/Kitchen Area
Exceptional
(27 reviews)

Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals

Saugerties

8% off
AU$9,060
for 7 nights, 1 home
AU$1,294 per night
includes taxes & fees
Beautiful Saugerties Rental -Pool, Fire Pit, close to HITS, Hiking, Festivals
Exterior
Living area
Private kitchen
Dining
Exceptional
(40 reviews)

5-Star New Barn Home - Music Studio, Views & Hot Tub

Saugerties

8% off
AU$8,599
for 7 nights, 1 home
AU$1,228 per night
includes taxes & fees
5-Star New Barn Home - Music Studio, Views & Hot Tub
Living room from back staircase
Interior
Exterior
Second Floor Bedroom #3 - Master Suite (see floor plans as reference)
Exceptional
(53 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

8% off
AU$10,398
for 7 nights, 1 home
AU$1,485 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Lobby
Living area
Living area
Living area
Excellent
(9 reviews)

The Race Mountain House

Sheffield

21% off
AU$6,898
for 7 nights, 1 home
AU$985 per night
includes taxes & fees
The Race Mountain House
Interior
Outdoor dining
Exterior detail
Dining
Exceptional
(10 reviews)

Church Des Artistes a Hudson Valley retreat

Kingston

8% off
AU$17,492
for 7 nights, 1 home
AU$2,499 per night
includes taxes & fees
Church Des Artistes a Hudson Valley retreat
Room
Exterior detail
Living area
Interior
Exceptional
(10 reviews)

Heart of the Village Victorian Saugerties NY

Saugerties

5% off
AU$3,962
for 7 nights, 1 home
AU$566 per night
includes taxes & fees
Heart of the Village Victorian Saugerties NY
Dining
Moose Lodge
Private kitchen
Room
Exceptional
(54 reviews)

Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge

Great Barrington

8% off
AU$21,571
for 7 nights, 1 room
AU$3,082 per night
includes taxes & fees
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Exterior
Interior
Dining
Property grounds
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$9,604
for 7 nights, 1 cabin
AU$1,372 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County
Living area
Private kitchen
Exterior
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
AU$8,157
for 7 nights, 1 home
AU$1,165 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Entry foyer
kitchen island w/reclaimed wood
view from the kitchen window
Our home sweet home!
Exceptional
(26 reviews)

TREEMENDOUS VIEWS COTTAGE

Amenia

8% off
AU$5,686
for 7 nights, 1 home
AU$812 per night
includes taxes & fees
TREEMENDOUS VIEWS COTTAGE
French Doors leading to a veranda offer a wonderful connection to the outdoors, making it the perfect spot to start your day with a cup of morning coffee or tea.
Dining
A Special Place for Your Special Times! 4 bedroom, 3.5 baths, Full Kitchen, Kitchenette, 2 Living Areas, 2 Dining Areas, Full access to backyard with dining area, fire pit with adirondack chairs, BBQ grill, hammock on 2 acres of land.
For those moments when you prefer a more private escape, we've created a tranquil area in the front yard.
Exceptional
(27 reviews)

Spacious 4BD Country Gem - Fire Pit & Chill Vibes

Highland

7% off
AU$4,112
for 7 nights, 1 home
AU$587 per night
includes taxes & fees
Spacious 4BD Country Gem - Fire Pit & Chill Vibes
View from the water
View from the Top Deck
Approaching the home
Dining Area view
Exceptional
(11 reviews)

Lakefront +pets +skiing +bbq +firepit +games

Copake

8% off
AU$3,950
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
Lakefront +pets +skiing +bbq +firepit +games
Interior
Terrace/patio
Room
Bathroom
Exceptional
(7 reviews)

New! Thoughtful and Cozy Craftsman Waiting for You! Walk to village center!

Saugerties

8% off
AU$4,092
for 7 nights, 1 home
AU$585 per night
includes taxes & fees
New! Thoughtful and Cozy Craftsman Waiting for You! Walk to village center!
Living Room
Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(52 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

8% off
AU$6,230
for 7 nights, 1 home
AU$890 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Pool
Exterior
Living area
Outdoor dining
Exceptional
(49 reviews)

Secluded family retreat within minutes of Woodstock village

Saugerties

8% off
AU$4,716
for 7 nights, 1 home
AU$674 per night
includes taxes & fees
Secluded family retreat within minutes of Woodstock village
Staircase
You will love dining and working in this rich and colorful room
The living room flows into the dining room.
A mudroom off the back leads to the large wooden deck
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

12% off
AU$4,350
for 7 nights, 1 home
AU$621 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Property grounds
Property grounds
Room
Property grounds
Exceptional
(17 reviews)

Hudson Valley’s Private Waterfront Camping Getaway

Lake Katrine

8% off
AU$2,330
for 7 nights, 1 unit
AU$333 per night
includes taxes & fees
Hudson Valley’s Private Waterfront Camping Getaway
Dining
Outdoor dining
Private kitchen
Room
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
AU$4,026
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Property grounds
Outdoor dining
Private kitchen
Exterior
Exceptional
(30 reviews)

Charming, Comfy House in Woodstock

Kingston

8% off
AU$2,939
for 7 nights, 1 home
AU$420 per night
includes taxes & fees
Charming, Comfy House in Woodstock
Private kitchen
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Open floor plan, natural light in a stylish space
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$4,140
for 7 nights, 1 home
AU$591 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Property grounds
Living area
Interior
Living area
Exceptional
(37 reviews)

Hidden Charm in Hudson Valley In Dutchess County

Salt Point

8% off
AU$5,576
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
Hidden Charm in Hudson Valley In Dutchess County
Interior
Property grounds
We highly recommend the Sauna
Property grounds
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,602
for 7 nights, 1 home
AU$515 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Pine Plains getaway

Learn about the unique charm of Pine Plains with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Pine Plains

Are you searching for top things to see and do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Pine Plains a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Lake Taghkanic State Park (8.2 mi / 13.1 km)
  • Millbrook Vineyards and Winery (9.7 mi / 15.7 km)
  • Catamount Ski Area (15.8 mi / 25.4 km)
  • Mohawk Mountain Ski Area (20.4 mi / 32.8 km)
  • Trevor Zoo (8.8 mi / 14.1 km)
  • Red Hook Golf Club (9 mi / 14.4 km)

Exploring the natural landscape of Pine Plains

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Pine Plains is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Harlem Valley Rail Trail (7.5 mi / 12.1 km)
  • Lake Taghkanic State Park (8.2 mi / 13.1 km)
  • Copake Lake (11.8 mi / 18.9 km)
  • Mount Frissell (12 mi / 19.3 km)
  • Great Falls (14.6 mi / 23.5 km)
  • Falling Waters Preserve (15.6 mi / 25.1 km)

How to get to and around Pine Plains

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 21.9 mi (35.3 km) from the city centre.

Frequently asked questions

What is the best area to stay in Pine Plains when booking a holiday rental?
When considering a holiday rental in Pine Plains, New York, the charming neighbourhood of the town centre stands out as an excellent choice. This area offers a quaint, community-focused atmosphere, making it great for those looking to immerse themselves in local culture. The town centre is home to a handful of delightful properties, ranging from cosy cottages to rustic homes, providing a variety of options for visitors.One of the top attractions nearby is the scenic Pine Plains Town Park, where you can enjoy leisurely walks or picnics amidst beautiful greenery. Additionally, the historical charm of the area is highlighted by the Pine Plains Museum, which showcases the rich heritage of the region. Staying in the town centre not only places you within easy reach of these attractions but also allows you to experience the warmth and friendliness of the local community.
Where are the best Pine Plains ski resort rentals?
For skiing near Pine Plains, the closest options are found at the nearby Catamount Ski Area in Massachusetts, which is approximately a 30-minute drive away. In Pine Plains, travellers can look for holiday rentals that provide a comfortable base for their skiing adventures. Many properties in this area are charming country houses or cottages, often set on spacious plots with scenic views of the surrounding landscape.These accommodations typically include amenities such as full kitchens, cozy living rooms with fireplaces, and outdoor spaces for relaxation after a day on the slopes. Some properties may also feature hot tubs, which are superb for unwinding in the evening. Additionally, the area boasts proximity to local dining options and shops, making it convenient for guests to stock up on supplies or enjoy a meal out.For those interested in exploring beyond skiing, the region offers beautiful hiking trails and opportunities for winter activities like snowshoeing. Rentals in this area often provide a rustic charm, allowing visitors to enjoy both the thrill of skiing and the tranquillity of the countryside.
What is the most popular type of holiday rental accomodation in Pine Plains?
In Pine Plains, holiday houses are the most popular type of holiday rental, with around 57 available throughout the area. These properties typically provide ample space and amenities, including fully equipped kitchens, multiple bedrooms, and outdoor areas such as decks or gardens, great for enjoying the tranquil surroundings. Additionally, there are several cottages, apartments, and cabins, each offering a unique charm and a cozy feel. Cottages and cabins often feature rustic decor and cozy living spaces, making them ideal for a relaxing getaway.
Are there any family house rentals in Pine Plains?
In Pine Plains, New York, family-friendly homes are readily available, with around 20 options scattered throughout the area. This charming locale offers a blend of rural charm and outdoor adventure, making it an excellent choice for families. Many of these properties provide spacious living areas, full kitchens for preparing meals, and outdoor spaces superb for children to play and explore. Guests can also expect amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.Nearby attractions include the scenic landscapes of the Taconic State Park, which is great for hiking, picnicking, and enjoying nature. The town itself features quaint shops and local eateries, adding to the quaint, family-friendly atmosphere.
Can I rent a holiday home with a pool or hot tub in Pine Plains?
In Pine Plains, New York, there are several holiday homes available for rent that feature pools and hot tubs. This charming area offers a picturesque rural setting, superb for a relaxing getaway. Many of these properties come equipped with private pools and inviting hot tubs, providing a great place for families or groups to unwind after a day of exploring the local countryside.Travellers can expect amenities such as spacious outdoor areas, patio furniture for al fresco dining, and fully equipped kitchens that allow for convenient self-catering. Additionally, some rentals may include features like fire pits and expansive gardens, enhancing the overall experience of enjoying the serene surroundings.
Are there pet-friendly house rentals in Pine Plains?
In Pine Plains, there are several pet-friendly house rentals available, with a total of 19 options for travellers to choose from. Many of these holiday homes come equipped with amenities such as spacious gardens or yards, allowing pets to roam freely. Inside, visitors can expect comfortable living spaces, fully equipped kitchens, and sometimes even outdoor patios or decks for enjoying the scenic surroundings.The area itself is known for its beautiful landscapes, making it ideal for outdoor activities with pets. Nearby, the Taconic State Park offers hiking trails where you can explore the natural beauty of the region alongside your furry companions. Pine Plains also features charming local shops and eateries that may welcome pets, enhancing the overall experience for those travelling with their animals.
Are there any remote work holiday rentals in Pine Plains?
In Pine Plains, New York, there are numerous options for remote work holiday rentals, with around 72 available for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated desk spaces, and comfortable chairs, ensuring a productive environment.Travellers can expect to find a variety of accommodations, ranging from charming cottages to spacious homes suitable for extended stays. Many rentals also feature inviting living areas, full kitchens for meal preparation, and outdoor spaces for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pine Plains?
In Pine Plains, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing a lovely outdoor space to relax and enjoy the surroundings. For those who enjoy a morning brew, most rentals come with coffee and tea makers. Additionally, some accommodations permit pets, making it easier for travellers to bring their furry friends along. The presence of blenders in several properties also indicates a focus on convenience and comfort, suiting guests who may want to whip up smoothies or other blended treats.
When is the best time to visit Pine Plains for a holiday rental?
The peak travel season in Pine Plains is during the summer months from June to August, with July being particularly popular among holidaymakers. This vibrant period draws visitors keen to enjoy the area's lush landscapes and outdoor activities, such as hiking, cycling, and exploring local parks. The warm weather, with temperatures typically ranging from 20 to 30 degrees Celsius, makes it an ideal time for picnics and leisurely strolls through the charming village.For those seeking a blend of tranquillity and beauty, consider visiting in October. This is a wonderful time to witness the stunning autumn foliage, as the landscape transforms into a tapestry of reds, oranges, and yellows. The crisp air and quieter environment provide a superb backdrop for scenic drives and exploring the local wineries, all while avoiding the hustle and bustle of peak season.
What are the top attractions in Pine Plains?
In Pine Plains, visitors can enjoy a blend of natural beauty and small-town charm. The nearby Taconic State Park offers a range of outdoor activities, including hiking trails, picnic areas, and scenic views of the Catskill Mountains. The park is great for nature enthusiasts looking to explore the local flora and fauna.Additionally, the quaint downtown area features local shops and cafes, providing a taste of the community's hospitality. For those interested in history, the Pine Plains Library holds a collection of local historical archives, making it a nice stop for a leisurely afternoon.
Are all fees included in the Pine Plains holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Pine Plains holiday homes with parking?
Stayz offers a wide selection of holiday homes in Pine Plains with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Pine Plains holiday homes?
You can find great discounts on holiday homes in Pine Plains on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Pine Plains holiday home booking on Stayz?
To find Pine Plains holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pine Plains?
A long-stay holiday home in Pine Plains is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pine Plains holiday home?
Book your Pine Plains holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pine Plains?
Prices for holiday homes in Pine Plains vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pine Plains to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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