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Compare 75 Cottages in Jacksonville with updated reviews, rates, and availability.

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (41)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Great Place to get away and have clean fresh air surround you!
Book now for a magical & peaceful fall stay before its too late!
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (131)
"This was one of our favorite family trips ever! So fun using the paddle boat and seeing the misty mornings and starry nights in the lake."
Great Place to get away and have clean fresh air surround you!
Perfect for a peaceful get away in clean fresh Vermont air!
Newly sided entire house and garage
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (70)
"What a lovely stay! The cabin was stocked with everything we needed and it was very clean and well organized. The photos don't quite do it justice. Peaceful lake views all day with mountains in the distance - what's not to like? We used the queen bedroom on the main floor and the bed was so very comfortable. We were there for two weeks, so we definitely used the kitchen - again, a well-planned space and well stocked. We hope to be there again!"
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
Livingroom - Woodburning stove and sleeper double size pull out couch.
Lake life at Woodford Cottage
9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Exterior
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Cozy Falls Brook Cabin: Hike & Swim On-site!
Living area
Cozy Falls Brook Cabin: Hike & Swim On-site!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Cozy Falls Brook Cabin: Hike & Swim On-site!
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Outdoor dining
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Charlemont Retreat on Chickley River w/ EV Charger
Living area
Charlemont Retreat on Chickley River w/ EV Charger
3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Exterior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Jacksonville Cabin w/ Wraparound Deck & Views
Terrace/patio
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Living area
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Cozy Treetop Hideaway Near Harriman Reservoir!
Exterior
Cozy Treetop Hideaway Near Harriman Reservoir!
3.0 star property
Cozy Treetop Hideaway Near Harriman Reservoir!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Exterior
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
'john's Farmhouse in Mount Snow' on 120 Acres!
Exterior
'john's Farmhouse in Mount Snow' on 120 Acres!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!
Near Hiking & Skiing: Home in Wilmington!
Living area
Near Hiking & Skiing: Home in Wilmington!
3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Private kitchen
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Wilmington Vacation Rental Near Hiking and Skiing!
Miscellaneous
Wilmington Vacation Rental Near Hiking and Skiing!
3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
Cozy 'green Mountain Chalet' in Putney Town
Living area
Cozy 'green Mountain Chalet' in Putney Town
3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
Exterior
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!
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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Other property types in Jacksonville

Jacksonville Cabin w/ Wraparound Deck & Views
Jacksonville Vacation Rental | 3BR | 2BA | 2,000 Sq Ft | Stairs Required
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (27)
"Very nice home on its own road, far from any neighbors, lovely location overlooking pond."
Jacksonville Cabin w/ Wraparound Deck & Views
Bright three-level home with water views, jetted tub, firepit, and pool table
Bright three-level home with water views, jetted tub, firepit, and pool table
8.4 out of 10, Very Good, (25)
"We stayed three nights here. Just the two of us. I felt the pictures were misleading. Much smaller than expected. Since it was just the two of us it was perfect. "
Bright three-level home with water views, jetted tub, firepit, and pool table
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (40)
"We stayed at Chris' mansion for my wedding this past weekend and it was everything I expected and more. Although it isn't a full service venue, the owner Chris was sooooo helpful in getting everything we needed for our wedding. He owns a restaurant as well and was able to provide all of our appetizers, servers and bartenders! We even had our rehearsal dinner at his bar down the street called Jax on Tap. The bartenders were absolutely amazing and made us feel so welcome. They even made a sign...
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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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