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Holiday Rentals in Pleasant Valley

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Holiday Rentals in Pleasant Valley

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (34)
"It was an absolutely darling rental with goats and a quiet calm surrounding area. Owner was super easy to communicate with"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (61)
"We came up from Brooklyn to see the hot air balloons with my parents and it was just what we needed. Our Host Glen is very gracious and helpful! We loved staying at the Farm. The church and the grounds are beautiful. Glen provided us with fresh eggs, milk and honey. We were also allowed to pick tomatoes from his garden. All very delicious. "
The Farm at Hyde Park
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (47)
"This property was very comfortable, clean and had everything we needed. I was able to visit with my West Point Cadet for a weekend and cook a meal for her and we had a lovely time. "
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Cabin in the heart of the Hudson Valley, Cabin 4
Outdoor dining
Cabin in the heart of the Hudson Valley, Cabin 4
8.8 out of 10, Excellent, (15)
"A bright and surprisingly well furnished space considering its "tiny house" appearance (refrigerator, microwave, coffeemaker, snacks). The bathroom looks newly renovated, is stylish and spacious. The location is quiet and private, as well as very convenient to Rte 9W. When there were communication glitches, Julie was very responsive. One note of caution: if you don't care for lilac/purple paint on the walls, you might want to choose one of her other cabins; I wouldn't paint my own walls that...
The price is €150
includes taxes & fees
29 Sept - 30 Sept
Cabin in the heart of the Hudson Valley, Cabin 4
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (82)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (7)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is €841
includes taxes & fees
29 Sept - 30 Sept
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Hamptons on the Hudson in South Saugerties
Terrace/patio
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (8)
"Communication with host was top notch. The home is beautifully decorated (however probably not young children friendly as furnishings are light and airy, lots of light colors). The pool is wonderful and gets great sun. One caveat, not a good fit if you have mobility issues (I don't, I like the stairs and the exercise! But it would be rough if you have bad knees). I loved the property and I say THANK YOU! Nicely appointed and decorated."
Hamptons on the Hudson in South Saugerties
Mountain View escape
Exterior
Mountain View escape
10.0 out of 10, Exceptional, (38)
"Everything about the property was perfect! I would highly recommend"
Mountain View escape
Esopus Creek modern Tiny house Retreat!
Property grounds
Esopus Creek modern Tiny house Retreat!
9.4 out of 10, Exceptional, (11)
"We were in town for a family gathering and this house was in a great location and was exactly as described."
The price is €208
includes taxes & fees
29 Sept - 30 Sept
Esopus Creek modern Tiny house Retreat!
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
Property grounds
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
9.4 out of 10, Exceptional, (11)
"We have a nice stay in Kingston! The apartment had everything we needed for four adults and our two dogs. The bathroom was clean and well stocked, the beds were comfortable and we were able to hang out in the living room and play games. The couch in the living room was very hard and it was hard to really get comfortable there, though it was fine to sit upright and play games! The location was close enough to everything we wanted to see, but not quite walkable so we ended up driving around quite...
The price is €230
includes taxes & fees
30 Sept - 1 Oct
Hot Tub - Fire Pit - BBQ - Hammock - Colonial
The Studio at the Inn at High Falls
Exterior
The Studio at the Inn at High Falls
8.0 out of 10, Very good, (21)
"Great communication with host. Stayed one night for event at Arrowood Farms (only 10 minutes away). Clean , nicely decorated studio with plenty of light. Lovely yard. Close to all local attractions and dining. Large shower. Great towels and toiletries.TV and A/C worked well. Appreciated the drinking water.Really cozy studio. Has frig, microwave and coffee maker.(also iron and hair dryer). A fabulous stay, although water pressure was a little low, but certainly not a deal breaker. Had people...
The price is €239
includes taxes & fees
30 Sept - 1 Oct
The Studio at the Inn at High Falls
Sexiest Lil Cabin in Saugerties, NY
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
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (19)
"Matt has a great modern set up for 2 people to stay with simple but effortless accommodations. We loved our week long stay as Matt anticipated everything we could need. Ample towels, all the soap and toiletries one could need as well as a comfortable minimalist aesthetic. It was everything we could have asked for including a fire pit which we didn’t actually use but was a great addition to our stay should we want to. It overall all excellent stay!"
The price is €217
includes taxes & fees
30 Sept - 1 Oct
Campfire Cottage: Fireplace, fire pit & no chores!
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Exterior
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
10.0 out of 10, Exceptional, (114)
"A comfortable if older home with lots of natural light in the woods near New Paltz and Mohonk. Outdoor table and chairs plus grill make summer great. Host was very responsive and helpful. House could use a comfortable chair or two."
Midcentury Modern Cabin Home in the Woods- Under 2 Hrs From NYC!
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Exterior
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, (78)
"My fiancé and I had an amazing stay at this cabin. Very quiet and peaceful and lots to do just on the property alone. The host Karen was very nice and welcoming, left us ice cream sundaes and set up a birthday sign for my fiancé on our arrival! Beautiful cabin and very private, we will definitely be back! "
Romantic Log Cabin on Privately-Owned Lake with Fireplace
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Smart TV
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, (26)
"The house was just as pictured. Past reviews were helpful. Knowing about the driveway in advance was helpful. It is an odd floorplan, but it worked out fine for us. The kitchen is lovely and had everything we needed. We were in the area for the Stormville antique show. The house is in a great location, central to many great attractions. "
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
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See all available properties in Pleasant Valley
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.
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Other types of properties in Pleasant Valley you may be interested in

Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.2 out of 10, Wonderful, (34)
"It was an absolutely darling rental with goats and a quiet calm surrounding area. Owner was super easy to communicate with"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Best Western Plus Kingston Hotel And Conference Center
Premium bedding, in-room safe, desk, iron/ironing board
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, (1001)
"Good stay…"
The price is €149
includes taxes & fees
3 Oct - 4 Oct
Best Western Plus Kingston Hotel And Conference Center
DoubleTree by Hilton Poughkeepsie
Bar (on property)
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, (1000)
"Front desk is very professional and attending. And the room were clean and had a nice scent "
The price is €130
includes taxes & fees
3 Oct - 4 Oct
DoubleTree by Hilton Poughkeepsie
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.

Frequently asked questions

Are there holiday rentals in Pleasant Valley?

Yes, there are holiday rentals in Pleasant Valley close to Innisfree Garden, or you can select a more secluded option if you're looking for a relaxing stay. Pleasant Valley is known for its shopping and restaurants. Make sure you have time to check out the parks while you're in the area.

What are some of the best holiday rentals that Pleasant Valley has to offer?

Lakeview Home 3 Private Beaches w/ Kayaks, on Squantz Pond: This holiday home rental outside of Pleasant Valley is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Pleasant Valley?

Choose from 8 Expedia holiday rentals in Pleasant Valley for a memorable holiday.

What’s there to see and do in Pleasant Valley?

Innisfree Garden and James Baird State Park are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Eleanor Roosevelt National Historic Site and Vassar College.

What are holiday rentals like in Pleasant Valley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasant Valley. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.