Jefferson Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Jefferson vacation rentals

Pool
Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre

Vacation Home in Jefferson

Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre
10.0 out of 10, Exceptional, (3)
"Small and cozy as advertised, perfect for a couple and hope to get back soon"
United States
Sean S.
The price is ￥24,774
￥63,783 total
includes taxes & fees
Dec 15 - Dec 16
Catskill Modern Tiny Escape Hot Tub Sauna Outdoor Theatre
Fridge, microwave, oven, stovetop
2 Bedroom Farm Stay

Mobile Home in Delhi

2 Bedroom Farm Stay
10.0 out of 10, Exceptional, (11)
"Thank you! Never slept better! "
United States
vivian
The price is ￥24,878
￥46,009 total
includes taxes & fees
Dec 20 - Dec 21
2 Bedroom Farm Stay
Interior
Cozy Cabin-Catskills secluded Mountain retreat

Cabin in Gilboa

Cozy Cabin-Catskills secluded Mountain retreat
2.0 star property
10.0 out of 10, Exceptional, (2)
"Small cabin in the woods, nicely appointed and clean. 20 minute drive to Windham for shopping and dining. Cabin secluded and quiet, very peaceful spot."
United States
Lili
The price is ￥18,348
￥44,234 total
includes taxes & fees
Dec 17 - Dec 18
Cozy Cabin-Catskills secluded Mountain retreat
Fridge, microwave, oven, stovetop
A world where time stands still, close to Belleayre Ski & Wedding venues.

Vacation Home in City Roxbury

A world where time stands still, close to Belleayre Ski & Wedding venues.
9.4 out of 10, Exceptional, (31)
"Beautiful house, clean and in a beautiful location. A perfect home for rest and enjoyment in nature"
United States
Janko S.
The price is ￥18,799
￥72,163 total
includes taxes & fees
Dec 15 - Dec 16
A world where time stands still, close to Belleayre Ski & Wedding venues.
Fridge, microwave, oven, stovetop
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Vacation Home in Hensonville

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
10.0 out of 10, Exceptional, (10)
"Very clean and comfortable for the five of us. Close to windham and all of its activities"
United States
Jonathan M.
The price is ￥21,691
￥49,623 total
includes taxes & fees
Dec 17 - Dec 18
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Fridge, microwave, oven, stovetop
Golden Meadows spacious Cabin with Fire-pit, near all baseball camps

Cabin in Davenport

Golden Meadows spacious Cabin with Fire-pit, near all baseball camps
10.0 out of 10, Exceptional, (19)
"Magical roomy Cabin! Everything was perfect thatnks so much, had a wonderful stay."
United States
Alexander K.
The price is ￥20,408
￥42,208 total
includes taxes & fees
Dec 15 - Dec 16
Golden Meadows spacious Cabin with Fire-pit, near all baseball camps
Exterior
Cozy Country Farmhouse Along the Catskill Scenic Trail

Vacation Home in Hobart

Cozy Country Farmhouse Along the Catskill Scenic Trail
10.0 out of 10, Exceptional, (127)
"We stay here year after year! It is always clean, quiet, and well stocked. It feels like home away from home. "
United States
Andrea P.
The price is ￥24,540
￥49,789 total
includes taxes & fees
Dec 21 - Dec 22
Cozy Country Farmhouse Along the Catskill Scenic Trail
Exterior
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Apartment in Windham

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
9.2 out of 10, Wonderful, (40)
"Great place for an incredible price. We would definitely stay here again."
United States
Jason
The price is ￥13,322
￥22,801 total
includes taxes & fees
Dec 14 - Dec 15
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Property grounds
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Vacation Home in Ashland

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
9.2 out of 10, Wonderful, (5)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is ￥35,338
￥61,891 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Property grounds
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

Vacation Home in Windham

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
9.0 out of 10, Wonderful, (54)
"Check in & checkout and communication super easy. Location is excellent. A/C and hot water great. For 4 guys on a 2 day golf trip it worked fine. "
United States
david d.
The price is ￥22,391
￥36,945 total
includes taxes & fees
Dec 18 - Dec 19
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Outdoor spa tub
Romantic Catskill Getaway | HotTub w/Mountain View

Cabin in Prattsville

Romantic Catskill Getaway | HotTub w/Mountain View
2.0 star property
10.0 out of 10, Exceptional, (2)
"We stayed at a small cabin in the Catskills hosted by Umi and Bill, and we absolutely loved it. The place was beautiful, cozy, and thoughtfully decorated. The views were stunning, and Umi and Bill went above and beyond by providing plenty of helpful materials videos and clear instructions on how to use everything in the cabin. Everything was easy to understand and made our stay completely stress-free. We had a great time and will definitely be returning!"
United States
Goncalo D.
The price is ￥32,229
￥64,652 total
includes taxes & fees
Dec 14 - Dec 15
Romantic Catskill Getaway | HotTub w/Mountain View
Exterior
1st Class Rentals Cooperstown New 3 Bedroom House

Vacation Home in Cooperstown

1st Class Rentals Cooperstown New 3 Bedroom House
3.5 star property
10.0 out of 10, Exceptional, (1)
"Fantastic place! Everything as advertised. "
United States
Douglas
The price is ￥66,083
￥75,335 total
includes taxes & fees
Dec 17 - Dec 18
1st Class Rentals Cooperstown New 3 Bedroom House
Terrace/patio
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Vacation Home in Durham

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
4.0 star property
10.0 out of 10, Exceptional, (2)
"Was close to where we were attending a wedding and big enough to house us all!"
United States
Paul m.
The price is ￥26,644
￥71,854 total
includes taxes & fees
Dec 14 - Dec 15
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Exterior detail
WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !

Vacation Home in Hensonville, Windham

WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !
10.0 out of 10, Exceptional, (16)
"Had a great day here during Presidents’ Day weekend. Tricia was an amazing host and has outstanding communication skills. How’s everything we needed for enjoyable stay. Strongly recommend."
United States
Tarun K.
The price is ￥65,440
￥123,345 total
includes taxes & fees
Dec 15 - Dec 16
WINDHAM HOME SLEEPS 10 - 1 MILE TO SLOPES !
TV, fireplace, stereo
West Elm Lodge near Skiing • Waterfront • Groups • Breweries

Vacation Home in West Kill

West Elm Lodge near Skiing • Waterfront • Groups • Breweries
9.8 out of 10, Exceptional, (9)
"We had a great stay over Presidents Day weekend with a group of 3 adults and 5 children. The house looks exactly like the photos, and I would go as far to say it's even better in person. Everything was well appointed and worked great, beds and bedding were extremely comfortable, host communication impeccable, and we were impressed with the overall vibe of the home. Thanks for a great stay!"
United States
Alexandra D.
The price is ￥54,973
￥117,881 total
includes taxes & fees
Dec 14 - Dec 15
West Elm Lodge near Skiing • Waterfront • Groups • Breweries
1 bedroom, free WiFi
GLASS MIRROR CABIN - HAUS WINDHAM

Condo in Windham

GLASS MIRROR CABIN - HAUS WINDHAM
8.0 out of 10, Very Good, (1)
The price is ￥42,536
￥53,647 total
includes taxes & fees
Jan 13 - Jan 14, 2026
GLASS MIRROR CABIN - HAUS WINDHAM
Outdoor spa tub
2 Min Walk to Windham Town | Hot Tub | Fire Pit

Vacation Home in Windham

2 Min Walk to Windham Town | Hot Tub | Fire Pit
10.0 out of 10, Exceptional, (1)
"It was amazing for a big family! Tons of space, and everything was very clean! The hosts were also very pleasant to deal with."
United States
Hadassah S.
The price is ￥40,511
￥95,917 total
includes taxes & fees
Jan 5 - Jan 6, 2026
2 Min Walk to Windham Town | Hot Tub | Fire Pit
2 bedrooms, WiFi, bed sheets
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Cabin in Roxbury

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
10.0 out of 10, Exceptional, (9)
"This cabin was the cutest. Lots of charm and character with a beautiful view! "
United States
Stephanie G.
The price is ￥22,437
￥40,963 total
includes taxes & fees
Dec 14 - Dec 15
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Property grounds
Modern Cabin by Windham/Hunter Mountains

Cabin in Jewett

Modern Cabin by Windham/Hunter Mountains
2.0 star property
Modern Cabin by Windham/Hunter Mountains
Terrace/patio
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

Cabin in Windham

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
10.0 out of 10, Exceptional, (5)
"Beautiful property, very accurately represented in listing photos. Very well stocked with every thing you need to host. Lots of fun activities to do in the home. Would definitely recommend"
United States
Andrea S.
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jefferson Hotel Reviews

Black Bear Lodge

Black Bear Lodge

10/10 Excellent
"Easy parking, pet friendly, this property is clean and comfortable. The location is scenic and rural."
Kathleen 2-night trip
Posted 2 days ago
Black Bear Lodge

Find out more about Jefferson

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

  • View our selection of featured holiday rentals in Jefferson
  • Use the map to find apartments and other holiday homes in the Jefferson neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Jefferson while they last

Look no further and take a look at our great range of rental properties in Jefferson!

Frequently asked questions

Can I find a vacation rental in Jefferson?

Yes, you can find vacation rentals near top local attractions in Jefferson, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Jefferson has to offer?

A'Neils Windham Ski Lodge & Family Retreat: You might like this vacation home rental near Jefferson. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Jefferson?

With 9 Expedia vacation rentals, you're sure to find just the right place for your Jefferson stay.

What can I see and do in Jefferson?

While exploring the area, visit family-friendly sights like Hobart Book Village, or get outside and enjoy nature at Village Green at Jefferson. Burnt-Rossman Hills State Forest and Maple Museum are other places to visit while you're in town.

What’s a vacation rental in Jefferson like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Jefferson. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.