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Jacksonville Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Jacksonville holiday rentals

Living area

1. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (5 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is HK$2,570
HK$4,697 total
includes taxes & fees
25 Aug - 26 Aug
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Exterior

2. 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, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is HK$1,671
HK$4,139 total
includes taxes & fees
31 Aug - 1 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Coffee/tea maker, fridge, microwave, stovetop

3. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
9.8 out of 10, Exceptional, (7 reviews)
"A beautiful, clean, and cozy stay. The modern space was bright and well-equipped with everything we needed, and the hot tub made it especially relaxing."
United States
Nicole H.
The price is HK$3,509
HK$6,197 total
includes taxes & fees
20 Aug - 21 Aug
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Smart TV, fireplace, video games, DVD player

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (61 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is HK$2,675
HK$6,392 total
includes taxes & fees
13 Aug - 14 Aug
Walk To Town, Hottub, Firepit, Games, Mt Snow
Private kitchen

5. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is HK$981
HK$2,056 total
includes taxes & fees
7 Sept - 8 Sept
The Studio with a View. Bring your dog, too!
Property grounds

6. A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is HK$1,883
HK$5,154 total
includes taxes & fees
13 Aug - 14 Aug
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Dining

7. 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, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is HK$1,852
HK$4,898 total
includes taxes & fees
26 Aug - 27 Aug
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Coffee/tea maker, fridge, microwave, oven

8. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (53 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is HK$2,779
HK$5,804 total
includes taxes & fees
16 Aug - 17 Aug
Spacious 5BR w/ Hot Tub & Games
Coffee/tea maker, fridge, microwave, oven

9. 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 HK$3,636
HK$9,136 total
includes taxes & fees
13 Aug - 14 Aug
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Smart TV, fireplace, books

10. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (6 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 HK$2,374
HK$5,491 total
includes taxes & fees
16 Aug - 17 Aug
5BR Berkshire Home Mins To The Mountain
Interior

11. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is HK$2,981
HK$5,127 total
includes taxes & fees
20 Aug - 21 Aug
3 Mi to Mount Snow: Spacious West Dover Home
Exterior

12. Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,138
HK$4,759 total
includes taxes & fees
23 Aug - 24 Aug
Bear Creek Cabin
Exterior

13. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin in a beautiful location. Host is amazing, very responsive. "
United States
Anonymous traveller
The price is HK$2,431
HK$3,937 total
includes taxes & fees
24 Aug - 25 Aug
The Greylock Cabin
Interior

14. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 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 HK$911
HK$1,605 total
includes taxes & fees
16 Aug - 17 Aug
Lovely 2nd Floor Apartment
Outdoor pool, a heated pool

15. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$534
HK$2,491 total
includes taxes & fees
31 Aug - 1 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

16. 10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK

10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is HK$2,095
HK$5,168 total
includes taxes & fees
17 Aug - 18 Aug
10 Mins to Mt Snow Golf Club-Game Room, Barrel Sauna, Hot Tub, Fire Pit, Dogs OK
Property grounds

17. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is HK$1,634
HK$3,726 total
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
Terrace/patio

18. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
West Dover
10.0 out of 10, Exceptional, (1 review)
"All good. "
United States
ken g.
The price is HK$2,479
HK$5,399 total
includes taxes & fees
20 Aug - 21 Aug
3 Mi to Mount Snow: Spacious West Dover Home
Coffee/tea maker, fridge, microwave, oven

19. Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
The price is HK$4,315
HK$7,855 total
includes taxes & fees
10 Sept - 11 Sept
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Property grounds

20. Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views

Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
Stamford
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful area and views of mountains, very gracious host "
United States
Donna E.
The price is HK$1,448
HK$2,659 total
includes taxes & fees
19 Aug - 20 Aug
Charming 3-bedroom Vermont house with outdoor Sauna and Mountain Views
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

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Great & comfortable place, good staff. Free (simple) breakfast! A pool, hot tub. And the incredible Mass Moca right there. Our second time here, & we’ll be back."
Floyd 3-night trip
Posted 1 hour ago
The Porches Inn at Mass MoCA

Find out more about Jacksonville

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

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

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

Frequently asked questions

Can I find a holiday rental in Jacksonville?

Yes, there are holiday rentals close to the most popular sights in Jacksonville, or you can select a more secluded option if you're looking for a relaxing stay. Jacksonville is known for its wineries and parks.

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

Bright three-level home with water views, jetted tub, firepit, and pool table: This highly rated holiday home rental in Jacksonville is located in the mountains, and has a fireplace, a garden and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of billiards or a pool table in this rental home to help you unwind.

How many holiday rentals are there in Jacksonville?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Jacksonville stay.

What’s there to see and do in Jacksonville?

While exploring the area, visit family-friendly sights like Brattleboro Bowl, or get outside and enjoy nature at Jacksonville Pond. H.O. Cook State Forest and Molly Stark State Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Jacksonville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Jacksonville. Holiday rentals feature extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.