Search Holiday Rentals in Pine Plains

Save an average of 15% on thousands of properties with Expedia Rewards

Become a member for free and get more than just a booking discount. Members also earn points towards their next trip.

Search over 2.9 million properties and 550 airlines worldwide.

Find properties with these dates

Tonight
May 2 - May 3
Tomorrow
May 3 - May 4
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Top Holiday Rentals in Pine Plains

Exterior
The Farm at Hyde Park
9.6 out of 10, Exceptional, (45)
"We booked the Chapel for a quick weekend to check out the FDR Home and other sights around Hyde Park and Dutchess County. The place was perfect for our needs! Glen was very helpful and communication was excellent. We loved that the property has chickens and a wild turkey."
The Farm at Hyde Park
Pool
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
8.8 out of 10, Excellent, (5)
"Stay, house, check in were all great. It was pretty far to Hunter mountain but the house was perfect for our little getaway!"
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Balcony
Micosta Leisure Inn
3.0 star property
8.8 out of 10, Excellent, (70)
"I needed a place to sleep while attending several events in the area and this was perfect; clean, safe, warm, great snacks. The only negative was the icy steps and deck. I had to break up the ice and clear with my boots. Place could use an electric kettle for tea. Other than that it was a great place for me and my elderly dog. "
The price is £112
per night
5 May - 6 May
Micosta Leisure Inn
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, (41)
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (28)
"We've stayed in a lot of home rentals - and across the board - this was the best place ever. The home was clean, nicely decorated and super comfortable. The hosts were easy to get a hold of and incredibly welcoming, leaving us with a generous basket of local treats. We loved the peaceful outdoor space and roamed all 40 acres. The pond was beautiful and if it had only been warmer we'd have jumped in the rowboat. We will be back for sure. A++ Thank you, Anna!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (29)
"The accommodations were excellent. We were a couple, but the house would be great for two couples. We loved the setting! The host has thought of everything, and the place is equipped to the max. Just bring yourself! Perfect location to explore the area."
Cozy Relaxing Retreat in Saugerties, NY
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Exactly as described. Clean & comfortable with all the amenities of home . Great for a long weekend getaway. Just a short drive from plenty of restaurants, store and attractions."
The price is £174
per night
13 May - 14 May
Mid-Century DJ’s Dream
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (64)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
1 bedroom, free WiFi, bed sheets
Romantic Luxury Chalet With Private Pool
10.0 out of 10, Exceptional, (259)
"Richard was very kind and thoughtful. The stay was very comfortable and Richard provided many ideas for things to in the vicinity. We will definitely consider staying here again if we're back in the area."
Romantic Luxury Chalet With Private Pool
Exterior
Sexiest Lil Cabin in Saugerties, NY
8.4 out of 10, Very good, (6)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY
Fridge, microwave, oven, stovetop
Romantic and Secluded Berkshire's Gem
10.0 out of 10, Exceptional, (9)
"My friends and I had an amazing time staying in the cozy cabin. 9 of us slept comfortably, the place was spotless, and so cute. We hope to visit again."
Romantic and Secluded Berkshire's Gem
Exterior
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
"The house is amazing, it delivers on everything stated in the listing and then some. This was our second time staying at Stephen's place and it just keeps getting better. Can't wait for the next one. If you love to listen and play music, its a must."
5-Star New Barn Home - Music Studio, Views & Hot Tub
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (74)
"For the groomsman it was perfect crazy fun."
Spectacular Short Term Vacation Rental in Kent
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons
9.8 out of 10, Exceptional, (78)
"I rented Big Sky for the weekend to celebrate my girlfriend’s birthday. This place was everything I could have asked for and more. Myra and Jerry were very accommodating and made sure we had everything we needed. The place itself was very charming and the views were as incredible as they described. It was an overall awesome experience, and I’m very thankful we rented Big Sky!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Private kitchen | Fridge, microwave, oven, stovetop
NEW The Art Loft in Kingston NY
9.6 out of 10, Exceptional, (4)
"The apartment was great and had a unique charm. Would recommend."
NEW The Art Loft in Kingston NY
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (15)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is £152
per night
15 May - 16 May
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (27)
"For a woodsy getaway close to real highways, here’s your spot. A good home base for local activities. Cute not chic, clean and functional. Chickens and goats on the property added a great farm with no work charm."
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Outdoor dining
Moose Lodge by AvantStay | Luxe Berkshires Escape
10.0 out of 10, Exceptional, (11)
"It was unique, with unusual amenities, like the home theater and fabulous game room. Our weather was wintery, so this was such a comfortable and fun way for the family to spend time together!"
Moose Lodge by AvantStay | Luxe Berkshires Escape
Property grounds
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is £199
per night
15 May - 16 May
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Don't see what you're looking for?
See all available properties in Pine Plains
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Pine Plains you may be interested in

Lobby
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, (1001)
"It was close to the event I was attending, Staff is very polite with the exception of cleaning ladies, who started to talk loudly in am without regard to people who might be still sleeping; Room was nice , clean but the window could not be closed all the way , so had to keep the heater on all night. Overall good enough stay."
The price is £125
per night
8 May - 9 May
Best Western Plus Kingston Hotel And Conference Center
Premium bedding, down duvets, Tempur-Pedic beds, laptop workspace
AutoCamp Catskills
3.5 star property
9.0 out of 10, Wonderful, (266)
"The property and our cabin was great but the housekeeping system needs a little attention. Our cabin was not serviced during our stay. We stayed Monday-Thursday and had to go to the main house for more toilet paper, Kleenex, and towels ourselves. Id like to respectfully offer a suggestion… It would be nice if perhaps these things were put in a bag and left on our doorstep each morning or evening so that we could have fresh towels etc. As guests, we could also place used towels in bags and...
The price is £182
per night
20 May - 21 May
AutoCamp Catskills
Reception
Hampton Inn Kingston
2.5 star property
9.0 out of 10, Wonderful, (1002)
"Beautiful place with very friendly staff definitely recommend "
The price is £126
per night
27 May - 28 May
Hampton Inn Kingston
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Pine Plains holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Plains holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pine Plains holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Pine Plains holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Plains. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pine Plains holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pine Plains holiday rentals we have selected for you start as low as £112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pine Plains rentals

At Expedia, we put the best Pine Plains holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Pine Plains rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pine Plains holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pine Plains. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Pine Plains?

Yes, there are holiday rentals close to the most popular sights in Pine Plains, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Pine Plains has to offer?

The Farm at Hyde Park: This holiday home rental outside of Pine Plains is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Pine Plains?

With 28 Expedia holiday rentals, you're guaranteed to find just the right place for your Pine Plains stay.

What can I see and do in Pine Plains?

Thompson Pond and Stissing Lake Park are a couple of scenic spots to enjoy the outdoors, whereas The Stissing Center is one of the cultural attractions. While here, Pine Plains Library and Gallatin Town Hall are other places worth a visit.

What are holiday rentals like in Pine Plains?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pine Plains. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.

Recent reviews of Pine Plains properties
Expedia verified reviews

Mirbeau Inn & Spa

Mirbeau Inn & Spa

5/5 Excellent
"10/10 would recommend. Worth every penny! Staff was wonderful, room was perfect, and the complimentary bathbomb and truffles were a nice touch. Loved the spa, hot tub, and cocktails. Also, easily the best breakfast I've ever had (french toast). Book now, you won't regret it!"
A verified traveller stayed at Mirbeau Inn & Spa
Posted 3 days ago
Mirbeau Inn & Spa