Samsonville Holiday Rentals

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Check prices for these dates

Tonight
13 Dec - 14 Dec
Tomorrow
14 Dec - 15 Dec
Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec

Our top choices for Samsonville holiday rentals

Property grounds
Streamside Cottage Half Mile to Town of Woodstock

Cottage in Woodstock

Streamside Cottage Half Mile to Town of Woodstock
10.0 out of 10, Exceptional, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
Streamside Cottage Half Mile to Town of Woodstock
Exterior
Starlite Motel

Aparthotel in Big Indian

Starlite Motel
2.5 star property
9.2 out of 10, Wonderful, (274)
"Awesome place to stay!"
United States
Earl
The price is HK$961
HK$1,077 total
includes taxes & fees
5 Jan - 6 Jan 2026
Starlite Motel
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Holiday Home in Kingston

Esopus Creek modern Tiny house Retreat!
9.8 out of 10, Exceptional, (62)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
The price is HK$1,156
HK$1,844 total
includes taxes & fees
11 Jan - 12 Jan 2026
Esopus Creek modern Tiny house Retreat!
TV, fireplace, stereo
Relaxing Catskill Mountain Cottage.

Cottage in West Shokan

Relaxing Catskill Mountain Cottage.
10.0 out of 10, Exceptional, (56)
"Wonderful experience and beautiful property."
United States
James B.
Relaxing Catskill Mountain Cottage.
Children’s area
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Cottage in woodstock

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.0 out of 10, Wonderful, (46)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
The price is HK$1,401
HK$2,415 total
includes taxes & fees
14 Dec - 15 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Fridge, microwave, oven, stovetop
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat

Holiday Home in Bearsville

Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
10.0 out of 10, Exceptional, (124)
"A beautiful house on a stunning property. Looking forward to coming back!"
United States
A. M.
Luxurious Woodstock Home Rental Catskill Mountains Views & Private Retreat
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Apartment in Kingston

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is HK$631
HK$1,752 total
includes taxes & fees
14 Dec - 15 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior
TRANQUIL MOUNTAIN SOLITUDE

Mobile Home in Pine Bush

TRANQUIL MOUNTAIN SOLITUDE
10.0 out of 10, Exceptional, (4)
"Such a quaint & cozy little hideaway! Hosts could not be more hospitable. Thank you for a great stay!"
United States
Michelle H.
The price is HK$960
HK$1,720 total
includes taxes & fees
20 Dec - 21 Dec
TRANQUIL MOUNTAIN SOLITUDE
Dining
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly

Cabin in Grahamsville

Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
9.4 out of 10, Exceptional, (36)
"Very well stocked. Beautiful, quiet location. Very comfortable. "
United States
Ladytiger
Catskill Retreat: Cozy Cabin with Cedar Hot Tub & Pet-Friendly
Exterior
Mountain View escape

Cottage in New Paltz

Mountain View escape
10.0 out of 10, Exceptional, (69)
"Really cute cottage with a view of Skytop and the mountains. Quiet location. Fully equipped kitchen. Enjoyed our stay very much. "
United States
barbara d.
Mountain View escape
Exterior
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains

Cabin in Claryville

Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
10.0 out of 10, Exceptional, (233)
"Very clean and well stocked cabin."
United States
Prachi P.
Claryville Cabin with 1,500 ft Trout River in the Catskill Mountains
Outdoor pool
Woodstock Historic Artist Estate - The Museum House

Holiday Home in Woodstock

Woodstock Historic Artist Estate - The Museum House
10.0 out of 10, Exceptional, (6)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
The price is HK$4,739
HK$7,949 total
includes taxes & fees
13 Jan - 14 Jan 2026
Woodstock Historic Artist Estate - The Museum House
The Cabin at Chichester in the Catskills Mountains

Cottage in Chichester

The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (189)
"Nice place"
United States
Ron G.
The Cabin at Chichester in the Catskills Mountains
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Holiday Home in new paltz

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
9.6 out of 10, Exceptional, (5)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
The price is HK$1,401
HK$5,526 total
includes taxes & fees
20 Dec - 21 Dec
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Exterior
The Studio at the Inn at High Falls

Holiday Home in High Falls

The Studio at the Inn at High Falls
8.0 out of 10, Very good, (33)
"Perfect location. Easy access to great surrounding area. Nice space. We had only one night. Wish it was longer!"
United States
loretta p.
The price is HK$875
HK$2,087 total
includes taxes & fees
20 Dec - 21 Dec
The Studio at the Inn at High Falls
Exterior
Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!

Holiday Home in Napanoch

Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!
2.0 star property
10.0 out of 10, Exceptional, (4)
"Wonderful stay, awesome house and great host. Super cozy vibes and perfect for friends/families."
United States
Beili C.
Shambhala Mountain Retreat: A chalet surrounded by forest. Relax & unwind!
4 bedrooms, iron/ironing board, WiFi
Mountain Peak Retreat - Pool - Hot Tub

Holiday Home in Ellenville

Mountain Peak Retreat - Pool - Hot Tub
10.0 out of 10, Exceptional, (6)
"This place is amazing, silence that’s what I need it, clean, pool, jacuzzi, view impressive "
United States
Jorge L.
Mountain Peak Retreat - Pool - Hot Tub
Exterior
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock

Holiday Home in Woodstock

Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
10.0 out of 10, Exceptional, (116)
"great property with lots of play/sleep/eat options for a large family. Loved mornings and nights on the large screened porch---our favorite spot. nice proximity to the town of Woodstock ."
United States
Jo C.
Stunning home with pool, spa, mountain views, sleeps up to 10, walk to Woodstock
Interior
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN

Holiday Home in Woodstock

HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
10.0 out of 10, Exceptional, (102)
"Amazing, large artist-type retreat. Great for our family getaway and being dog friendly is a huge plus for us. Minutes from Woodstock and not far from other attractions made for easy entertainment.We didn’t use the fireplace or pool, but did use the hot tub and it was great.All together, we really enjoyed our stay and Bill was great answering my questions and helping out when we needed it."
United States
Ashley E.
HOT TUB w/ POOL, STREAM on 7 Acres, JUST 2 MINUTES FROM TOWN
Exterior
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley

Chalet in New Paltz

Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson Valley
10.0 out of 10, Exceptional, (12)
"Absolutely stunning A-frame! Super spacious, very clean/tidy, lots of room to hang inside, downstairs or have a fire outdoors. Beautiful area not far from New Paltz. We had such a fantastic time and would recommend this place to any group staying in the area! "
United States
Danielle O.
The price is HK$4,028
HK$7,459 total
includes taxes & fees
16 Dec - 17 Dec
Spacious A-Frame w/ Game Room, Fire Pit & Modern Comforts in Hudson 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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Top Samsonville Hotel Reviews

Hutton Brickyards Riverfront Hotel + Venue

Hutton Brickyards Riverfront Hotel + Venue

10/10 Excellent
"Beautiful rooms and incredibly friendly staff. We will be back!!"
Alex 1-night trip
Posted 1 day ago
Hutton Brickyards Riverfront Hotel + Venue

Find out more about Samsonville

Search for holiday rentals in Samsonville on Expedia! You can easily find your home rentals, villas, holiday apartments in Samsonville using one of the methods below:

  • View our selection of featured holiday rentals in Samsonville
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Look no further and take a look at our great range of rental properties in Samsonville!

Frequently asked questions

Are there holiday rentals in Samsonville?

Yes, there are holiday rentals close to the most popular sights in Samsonville, or you can select a more secluded option if you're looking for a relaxing stay. Samsonville is known for its entertainment choices and ski areas. Make sure you have time to check out the mountain views and restaurants during your trip.

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

Esopus Creek modern Tiny house Retreat!: This holiday home rental outside of Samsonville is located on a river, and has a fireplace, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Samsonville?

Explore the area and cultural attractions such as Mount Tremper Arts, or visit one of the family-friendly sights such as Straus Center - Frost Valley YMCA. In the wider area, you’ll find Catskill State Park and Slide Mountain.

What are holiday rentals like in Samsonville?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Samsonville. Holiday rentals offer extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for a small group gathering.