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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Jacksonville holiday homes

An aerial view of a house surrounded by a forest with autumn foliage.

1. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is £422
includes taxes & fees
28 Oct - 29 Oct
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

2. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is £153
includes taxes & fees
13 Oct - 14 Oct
The Eagles Wing at The CHM - Private Apartment
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

3. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is £423
includes taxes & fees
26 Oct - 27 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

4. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is £525
includes taxes & fees
28 Oct - 29 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A bedroom with a skylight, a bed with floral bedding, a bedside table, and a nightstand.

5. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is £82
includes taxes & fees
2 Nov - 3 Nov
Cozy Vermont Tiny Home Get Away
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

6. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is £603
includes taxes & fees
5 Oct - 6 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

7. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is £578
includes taxes & fees
9 Oct - 10 Oct
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

8. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is £181
includes taxes & fees
22 Oct - 23 Oct
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

9. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is £167
includes taxes & fees
25 Oct - 26 Oct
Private bed with En-suite bathroom Marigold Room
A bedroom with a bed, bedside tables, a window, and a radiator.

10. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is £353
includes taxes & fees
6 Oct - 7 Oct
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

11. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
Modern Mount Snow Gnarvana - Steps to Carinthia
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

12. Greylock Cabin

Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is £350
includes taxes & fees
29 Oct - 30 Oct
Greylock Cabin
A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

13. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is £528
includes taxes & fees
6 Oct - 7 Oct
5BR Berkshire Home Mins To The Mountain
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

14. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is £534
includes taxes & fees
4 Oct - 5 Oct
Spacious 5BR w/ Hot Tub & Games
A hallway with wooden flooring, white walls, and a bed in the background.

15. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is £329
includes taxes & fees
4 Oct - 5 Oct
Cozy private 2 bed apartment in Shelburne Falls
A modern kitchen with a built-in fireplace, wine storage, and a dining area with wooden furniture.

16. Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is £884
includes taxes & fees
7 Oct - 8 Oct
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
A house with a deck, two Adirondack chairs, a glass-top table, and a barbecue grill.

17. Spacious Vermont Farmhouse | 3 Mi to Mount Snow

Spacious Vermont Farmhouse | 3 Mi to Mount Snow
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is £619
includes taxes & fees
4 Oct - 5 Oct
Spacious Vermont Farmhouse | 3 Mi to Mount Snow
A kitchen with white cabinets, a wooden dining table, and pendant lights.

18. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is £362
includes taxes & fees
14 Oct - 15 Oct
A roomy remodeled retreat close to MassMoCA
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

19. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
The price is £468
includes taxes & fees
7 Oct - 8 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious kitchen with a large island, wooden ceiling beams, and a view to the outside.

20. 5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton

5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
Stratton
10.0 out of 10, Exceptional, (20 reviews)
"Great spot for a large group. "
United States
Brian G.
The price is £828
includes taxes & fees
1 Nov - 2 Nov
5BR Retreat w/ Hot Tub - Sleeps 12 in Stratton
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 Jacksonville Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"The room was clean and spacious."
Wendy 1-night trip
Posted 9 hours ago
Hampton Inn Brattleboro

Find out more about Jacksonville

Jacksonville Holiday Homes information

Number of reviews
365
Accommodation
428 Holiday Homes
Lowest Price
£82
Highest Price
£884