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Holiday homes in Jacksonville You’ll Love

Top-Rated Jacksonville Holiday homes for Every Budget and Style!

Looking for a holiday home in Jacksonville (Vermont)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Jacksonville.

We found 17 Holiday-homes in Jacksonville and the surrounding area (within 30 miles)

Family Winter Retreat with Hot Tub 14 Mi to Slopes! in Whitingham, USA

Family Winter Retreat with Hot Tub 14 Mi...

Holiday home in Whitingham near Jacksonville, Vermont
Family Winter Retreat with Hot Tub 14 Mi to Slopes! offers accommodations in Whitingham, 12 miles from Molly Stark State Park and 19 miles from Mount ...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $1.071.09 Show details »

Hoot Owl Hollow in Jacksonville, USA

Hoot Owl Hollow

Holiday home in Jacksonville, Vermont
This vacation home offers accommodations with a balcony and free Wifi.
  • Parking
  • Sauna

Exceptional 1 Reviews 10.0

from $414.94 Show details »

Cozy Southern Vermont Home with On-Site Trails in Whitingham, USA

Cozy Southern Vermont Home with On-Site...

Holiday home in Whitingham near Jacksonville, Vermont
The property is around 31 miles from The Clark Art Institute, 12 miles from Molly Stark State Park, and 19 miles from Mount Snow Resort.
  • Parking

Passable 1 Reviews 5.0

from $385.28 Show details »

14mi to Mt. Snow! Arcade, Private Suite, King Bed! in Whitingham, USA

14mi to Mt. Snow! Arcade, Private Suite,...

Holiday home in Whitingham near Jacksonville, Vermont , 440 Ginny Morse Road
31 miles from Bennington Battle Monument in Whitingham, 14mi to Mt.
  • Parking
  • Pets allowed
  • Family rooms
  • Allergy-free room
  • Kids' outdoor play equipment

Exceptional 4 Reviews 9.5

from $441.97 Show details »

Home 15 Mi to Berkshire East and Mount Snow! in Whitingham, USA

Home 15 Mi to Berkshire East and Mount S...

Holiday home in Whitingham near Jacksonville, Vermont
Home 15 Mi to Berkshire East and Mount Snow! is located in Whitingham, just 30 miles from The Clark Art Institute and 30 miles from Bennington Museum.
  • Parking

no reviews

from $337.92 Show details »

Sadawga Springs Retreat in Whitingham, USA

Sadawga Springs Retreat

Holiday home in Whitingham near Jacksonville, Vermont , 6658 Vermont Route 100
Sadawga Springs Retreat is a recently renovated vacation home in Whitingham where guests can make the most of the free bikes and garden.
  • Parking
  • Restaurant
  • Family rooms

Fabulous 23 Reviews 8.7

from $81.00 Show details »

Log Cabin Escape in Jacksonville, USA

Log Cabin Escape

Holiday home in Jacksonville, Vermont
Log Cabin Escape offers accommodations in Jacksonville, 30 miles from Bennington Battle Monument and 29 miles from Bennington Museum.
  • Parking

Good 9 Reviews 7.0

from $220.49 Show details »

Cozy Log Cabin - Dog Friendly in Halifax, USA

Cozy Log Cabin - Dog Friendly

Holiday home in Halifax near Jacksonville, Vermont , 886 Brook Road
Cozy Log Cabin - Dog Friendly is located in Halifax, just 7.9 miles from Molly Stark State Park and 22 miles from Fort Dummer State Park.
  • Parking
  • Pets allowed

Exceptional 15 Reviews 9.7

from $216.18 Show details »

Vermont Ski Home Lake Home in Jacksonville, USA

Vermont Ski Home Lake Home

Holiday home in Jacksonville, Vermont , 268 North Ryder Pond Road
28 miles from Bennington Battle Monument in Jacksonville, Vermont Ski Home Lake Home provides accommodations with access to a hot tub.
  • Parking
  • Family rooms
  • Kids' outdoor play equipment

no reviews

from $61.00 Show details »

Jacksonville Cabin with Wraparound Deck and Views in Jacksonville, USA

Jacksonville Cabin with Wraparound Deck...

Holiday home in Jacksonville, Vermont
Jacksonville Cabin with Wraparound Deck and Views offers accommodations in Jacksonville, 29 miles from Bennington Battle Monument and 31 miles from St...
  • Parking

Exceptional 2 Reviews 10.0

from $263.04 Show details »

Sugarwood Farmhouse in Wilmington, USA

Sugarwood Farmhouse

Holiday home in Wilmington near Jacksonville, Vermont
Sugarwood Farmhouse is located in Wilmington, just 28 miles from Stratton Mountain and 25 miles from Bennington Museum.
  • Parking
  • Pets allowed

no reviews

from $52.00 Show details »

Whistling Peak in Wilmington, USA

Whistling Peak

Holiday home in Wilmington near Jacksonville, Vermont
Whistling Peak offers accommodations in Wilmington, 29 miles from Stratton Mountain and 25 miles from Bennington Museum.
  • Parking

Very good 2 Reviews 8.5

from $301.71 Show details »

Beautiful Home on 22 Acres with Ponds, Game Room, Hot Tub and Central Air in Wilmington, USA

Beautiful Home on 22 Acres with Ponds, G...

Holiday home in Wilmington near Jacksonville, Vermont , 419 Shearer Hill Road
Beautiful Home on 22 Acres with Ponds, Game Room, Hot Tub and Central Air is a recently renovated vacation home in Wilmington where guests can make th...
  • Parking
  • Pets allowed
  • Family rooms
  • Kids' outdoor play equipment

no reviews

from $59.00 Show details »

Spacious Wilmington Cabin Walk to Lake in Wilmington, USA

Spacious Wilmington Cabin Walk to Lake

Holiday home in Wilmington near Jacksonville, Vermont
Spacious Wilmington Cabin Walk to Lake offers accommodations in Wilmington, 26 miles from Bennington Battle Monument and 28 miles from Stratton Mounta...
  • Parking
  • Pets allowed

Exceptional 1 Reviews 10.0

from $451.25 Show details »

Little Red in Wilmington, USA

Little Red

Holiday home in Wilmington near Jacksonville, Vermont
Little Red offers accommodations in Wilmington, 25 miles from Bennington Museum and 26 miles from Southern Vermont College.
  • Parking
  • Pets allowed

No reviews yet 1 Reviews 1.0

from $159.08 Show details »

Lake Raponda Ski Cabin in Wilmington, USA

Lake Raponda Ski Cabin

Holiday home in Wilmington near Jacksonville, Vermont , 12 Gates Lane
Lake Raponda Ski Cabin offers accommodations in Wilmington, 24 miles from Stratton Mountain and 26 miles from Bennington Battle Monument.
  • Parking
  • Family rooms

no reviews

from $72.00 Show details »

Charming Wilmington Cabin, 8 Mi to Mt Snow! in Wilmington, USA

Charming Wilmington Cabin, 8 Mi to Mt Sn...

Holiday home in Wilmington near Jacksonville, Vermont
Charming Wilmington Cabin, 8 Mi to Mt Snow! is located in Wilmington, just 26 miles from Bennington Battle Monument and 25 miles from Bennington Museu...
  • Parking

Very good 1 Reviews 8.0

from $225.19 Show details »

Number of Holiday homes in Jacksonville 17
Number of guest ratings 16
Average price per night $315.00
Lowest price per night $50,00
Highest price per night $1.342,92

Top 10 Cheapest Holiday-homes in Jacksonville

Discover the Cheapest Holiday-homes in Jacksonville – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Jacksonville

Check out the Most Booked Holiday-homes in Jacksonville – Based on Guest Popularity.

Holiday homes in Jacksonville (Vermont), comfortable and familiar

Staying in a holiday or vacation home in Jacksonville can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Jacksonville for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Jacksonville should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com