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38 Houses

Great rentals within 20 miles that match your search

Distance approx 5.4 km from Jacksonville Show on Map

37

Spacious Wilmington Home w/ Game Room & Deck!

Vermont / Wilmington

Wilmington house

6 22 min stay varies

  • 6 bedrooms
  • sleeps 22
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$172

Responds fast!
avg. 11 minutes

Price per night from

$172

Distance approx 11.35 km from Jacksonville

31

Classic, dog-friendly cabin in the woods w/ private deck

Vermont / Dover

Dover house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$123

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$123

Distance approx 5.55 km from Jacksonville Show on Map

10

#B40: 99 North Road B040-03

Vermont / Wilmington

Wilmington villa

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$413

Price per night from

$413

Distance approx 16.87 km from Jacksonville

(2) Excellent 

41

Apartment walking distance to Mass MoCa!!

Berkshires / North Adams

North Adams apartment

2 10 min stay varies

  • 2 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Car not necessary

Price per night from

$201

Price per night from

$201

Distance approx 2.53 km from Jacksonville Show on Map

38

'John's Farmhouse in Mount Snow' on 120 Acres!

Vermont / Whitingham

Whitingham house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$344

Responds fast!
avg. 11 minutes

Price per night from

$344

Distance approx 6.78 km from Jacksonville Show on Map

17

Beautiful Cabin in a Peaceful 4 Season Resort with Club House Amenities

Vermont / Wilmington

Wilmington chalet

6 15 2 nights min

  • 6 bedrooms
  • sleeps 15
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Pet Friendly

Price per night from

$367

Price per night from

$367

Distance approx 5.55 km from Jacksonville Show on Map

10

#274: 28 Old Witness Tree Lane 274-01

Vermont / Wilmington

Wilmington villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$275

Price per night from

$275

Distance approx 5.55 km from Jacksonville Show on Map

10

#C230: 129 East Brook Crossing C230-03

Vermont / Wilmington

Wilmington villa

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$413

Price per night from

$413

Distance approx 7.99 km from Jacksonville Show on Map

10

#A59: 88 Howes Loop A059-02

Vermont / Wilmington

Wilmington villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$241

Price per night from

$241

Distance approx 5.55 km from Jacksonville Show on Map

10

#84: 18 Spring Court 084-01

Vermont / Wilmington

Wilmington villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$275

Price per night from

$275

Distance approx 5.55 km from Jacksonville Show on Map

10

#B109: 19 View Road B109-04

Vermont / Wilmington

Wilmington villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$172

Price per night from

$172

Distance approx 11.08 km from Jacksonville

(174) Excellent 

37

Unique People & Pet-Welcoming Country Haven

Berkshires / Charlemont

Charlemont apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly
“Cozy little spot, kid and definitely dog friendly” We brought our Cavalier with us and had a great time at the cottage. It was clean and gave us tons of room. Would definitely stay again.
…see more

Price per night from

$149

Price per night from

$149

Distance approx 9.1 km from Jacksonville Show on Map

(5) Excellent 

28

Condo on Haystack/Hermitage Ski Mountain

Vermont / Wilmington

Wilmington condo

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Ski
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 7.98 km from Jacksonville Show on Map

10

#585: 12 Lilla Lane 585-02

Vermont / Wilmington

Wilmington house

3 12 min stay varies

  • 3 bedrooms
  • sleeps 12
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$241

Price per night from

$241

Distance approx 5.55 km from Jacksonville Show on Map

9

#B55: 9 Corner Lane B055-02

Vermont / Wilmington

Wilmington villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$241

Price per night from

$241

Distance approx 7.1 km from Jacksonville Show on Map

10

#C184: 49 Low Land Loop C184-03

Vermont / Wilmington

Wilmington villa

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$413

Price per night from

$413

Distance approx 5.55 km from Jacksonville Show on Map

10

#627: 31 Howes Loop 627-02

Vermont / Wilmington

Wilmington villa

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Ask about children
  • Ask about pets

Price per night from

$722

Price per night from

$722

Distance approx 10.89 km from Jacksonville

10

Mount Snow 6BR+ Indoor Hot Tub, Sauna, Pool Table, FANTASY Ski Home

Vermont / Dover

Dover house

6 18 3 nights min

  • 6 bedrooms
  • sleeps 18
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$916

Price per night from

$916

Distance approx 12.01 km from Jacksonville

(2) Excellent 

35

Ski-in/ski-out condo with shared pool, hot tub & sauna - great location!

Vermont / Dover

Dover house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$154

Responds fast!
avg. 1 hour 47 minutes

Price per night from

$154

Distance approx 4.23 km from Jacksonville Show on Map

(1) Excellent 

7

PARADISE on EARTH! - Historic 4BR Farmhouse

Vermont / West Halifax

West Halifax house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$328

Price per night from

$328

Distance approx 15.74 km from Jacksonville

(1) Excellent 

21

Lake House in Berkshires

Berkshires / North Adams

North Adams cottage

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$121

Price per night from

$121

Distance approx 13.92 km from Jacksonville

(9) Excellent 

11

Charming Affordable Home for groups up to 14

Massachusetts / Shelburne Falls

Shelburne Falls house

7 14 2 nights min

  • 7 bedrooms
  • sleeps 14
  • 2 nights min
  • Ask about children
  • Car not necessary
  • Ask about pets
“Beautiful house in beautiful village!” Thank you for the use of your beautiful house. It was perfect for our wedding weekend. Everyone was very comfortable and had a great time. Looking forward to coming back again in the future.
…see more

Price per night from

$573

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$573

Distance approx 18.94 km from Jacksonville

(1) Excellent 

12

Classic New England Farm House

New Hampshire / Chesterfield

Chesterfield b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly

Price per night from

$52

Price per night from

$52

Distance approx 5.55 km from Jacksonville Show on Map

10

#210: 289 Chimney Hill Road 210-02

Vermont / Wilmington

Wilmington villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$241

Price per night from

$241

Distance approx 6.74 km from Jacksonville Show on Map

24

Cabin w/Deck - Mins to Mt. Snow & Lake Raponda!

Vermont / Wilmington

Wilmington log cabin

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly

Price per night from

$155

Responds fast!
avg. 11 minutes

Price per night from

$155

Distance approx 4.9 km from Jacksonville Show on Map

23

Lakeside Year Round Totally Renovated Home

Vermont / Wilmington

Wilmington house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$687

Price per night from

$687

Distance approx 8.19 km from Jacksonville Show on Map

9

Private Mountain Getaway

Vermont / Dover

Dover house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$138

Responds fast!
avg. 3 hours 47 minutes

Price per night from

$138

Distance approx 9.15 km from Jacksonville

(8) Excellent 

7

Berkshire Getaway

Berkshires / North Adams

North Adams cottage

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Pet Friendly
“peace and quiet!” This cottage is in a private, peaceful setting. We very much enjoyed our stay. We spent time at the Mass. Museum of Contemporary art in nearby North adams. We visited the summit of Mount Greylock, which was beautiful. We found our ho
…see more

Price per night from

$172

Price per night from

$172

Distance approx 11.61 km from Jacksonville

20

Casual lux near Hermitage Club & Four Columns Inn

Vermont / South Newfane

South Newfane villa

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 10 mi
  • Ski
  • Ask about children

Price per night from

$1,723

Price per night from

$1,723

Distance approx 16.6 km from Jacksonville

37

3 BR apartment, walking distance to Mass MoCa

Berkshires / North Adams

North Adams apartment

3 15 min stay varies

  • 3 bedrooms
  • sleeps 15
  • min stay varies
  • Ski
  • Child Friendly
  • Car not necessary

Price per night from

$212

Price per night from

$212

Distance approx 15.99 km from Jacksonville

(6) Excellent 

6

Retreat in the Woods

Berkshires / Savoy

Savoy house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Suitable for children age 5+

Price per night from

$229

Price per night from

$229

Distance approx 5.55 km from Jacksonville Show on Map

7

#C211: 114 East Brook Crossing C211-03

Vermont / Wilmington

Wilmington villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Ask about children
  • Pet Friendly

Price per night from

$413

Price per night from

$413

Distance approx 11.05 km from Jacksonville

(1) Excellent 

16

Balsam Cottage 4BR, Hot Tub, Pool Table, Fireplace - 5 minutes to the slopes

Vermont / Dover

Dover house

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Ski
  • Child Friendly
  • Pet Friendly

Price per night from

$573

Price per night from

$573

Distance approx 6.77 km from Jacksonville Show on Map

9

#B83: 24 Meadow View Rd B083-04

Vermont / Wilmington

Wilmington house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$172

Price per night from

$172

Distance approx 13.38 km from Jacksonville

9

MT SNOW NEW SKI HOME W/E-WEEK-MONTHLY or SEASON 3 BR 2 Bath 1.1 TO Mtn parking

Vermont / Dover

Dover house

3 7 4 nights min

  • 3 bedrooms
  • sleeps 7
  • 4 nights min
  • Ski
  • Child Friendly

Price per night from

$458

Price per night from

$458

Distance approx 5.55 km from Jacksonville Show on Map

10

#389: 8 Bear Lair Lane 389-02

Vermont / Wilmington

Wilmington villa

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ask about children
  • Pet Friendly

Price per night from

$241

Price per night from

$241

Distance approx 9.65 km from Jacksonville

(7) Excellent 

5

Vermont Log Cabin available for weekend and weekly

Vermont / Guilford

Guilford log cabin

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Pet Friendly
“Hidden Gem” My boyfriend and I had the pleasure of staying at this beautiful cabin a couple of weeks ago and honestly, I can't say enough good things about it! For starters, it is gorgeous both inside and out and much bigger than we had anticipated.
…see more

Price per night from

$126

Price per night from

$126

Distance approx 15.71 km from Jacksonville

(9) Very Good 

22

Flight's End-A Country Home with Babbling Brook

Massachusetts / Hawley

Hawley house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.
…see more

Price per night from

$172

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$172