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92 Houses

(1) Excellent 

20

Renovated Barn

Connecticut / Taconic

Taconic house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$403

Responds fast!
avg. 32 minutes

Price per night from

$403

Great rentals within 20 miles that match your search

Distance approx 1.46 km from Taconic Show on Map

(1) Excellent 

37

Charming 2+2 Lakeside Cottage on Best Lake in CT

Connecticut / Salisbury

Salisbury cottage

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$207

Price per night from

$207

Distance approx 8.27 km from Taconic Show on Map

11

Beautiful Cottage at the foot of the Berkshires

New York / Copake Falls

Copake Falls cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$202

Price per night from

$202

Distance approx 19 km from Taconic

28

Hudson Valley Cabin - Romantic & Secluded Log Cabin with Private Lake - 85 acres

New York / Stanfordville

Stanfordville log cabin

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$259

Price per night from

$259

Distance approx 6.27 km from Taconic Show on Map

(1) Excellent 

13

Lake House

Connecticut / Lakeville

Lakeville house

5 9 2 nights min

  • 5 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$690

Price per night from

$690

Distance approx 15.37 km from Taconic

(1) Excellent 

18

Hillhouse Log Cabin

New York / Hillsdale

Hillsdale log cabin

3 13 2 nights min

  • 3 bedrooms
  • sleeps 13
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe
…see more

Price per night from

$489

Price per night from

$489

Distance approx 11.3 km from Taconic

24

Rustic Berkshires Cottage w/ Views of Lake Buel!

Berkshires / New Marlborough

New Marlborough cottage

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Pet Friendly

Price per night from

$127

Responds fast!
avg. 26 minutes

Price per night from

$127

Distance approx 19.37 km from Taconic

7

Secluded House in the Woods w/ Year Round Hot Tub

New York / Red Hook

Red Hook house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$230

Price per night from

$230

Distance approx 17.68 km from Taconic

(1) Excellent 

17

Restored 1886 Eyebrow Colonial

Berkshires / Stockbridge

Stockbridge house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$246

Price per night from

$246

Distance approx 13.97 km from Taconic

(2) Excellent 

24

Country Elegance in the Berkshires

Berkshires / Great Barrington

Great Barrington house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Nearest beach 0 mi
  • Child Friendly
  • Air conditioning

Price per night from

$747

Responds fast!
avg. 2 hours 36 minutes

Price per night from

$747

Distance approx 9.78 km from Taconic

(2) Excellent 

14

Newly Renovated Lakefront Getaway on Robinson Pond

New York / Copake

Copake house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$230

Responds fast!
avg. 2 hours 51 minutes

Price per night from

$230

Distance approx 14.8 km from Taconic

(4) Very Good 

18

Lakefront Berkshires Ski/Summer House, Great Views

Berkshires / Great Barrington

Great Barrington house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$213

Price per night from

$213

Distance approx 5.55 km from Taconic Show on Map

(5) Excellent 

10

Apple Cottage

Berkshires / Sheffield

Sheffield farmhouse

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$431

Responds fast!
avg. 3 hours 22 minutes

Price per night from

$431

Distance approx 16.7 km from Taconic

48

Total Privacy! Tanglewood Retreat With Berkshire Views!

New York / Hillsdale

Hillsdale house

5 14 2 nights min

  • 5 bedrooms
  • sleeps 14
  • 2 nights min
  • Ask about children

Price per night from

$690

Price per night from

$690

Distance approx 6.61 km from Taconic Show on Map

(1) Excellent 

11

Riverwood - Cozy Carriage House in the Woods

Connecticut / Falls Village

Falls Village apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$259

Price per night from

$259

Distance approx 13.55 km from Taconic

30

Evergreen Pines Country Estate Villa

New York / Ancram

Ancram house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$2,299

Price per night from

$2,299

Distance approx 11.94 km from Taconic

(14) Excellent 

Certificate of Excellence

55

RiverSong Suite In The Berkshires

Berkshires / North Egremont

North Egremont apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Air conditioning

Certificate of Excellence

Price per night from

$218

Responds fast!
avg. 35 minutes

Price per night from

$218

Distance approx 14.85 km from Taconic

23

Spacious Lakeside Berkshire Home

Berkshires / Monterey

Monterey house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$460

Responds fast!
avg. 3 hours 48 minutes

Price per night from

$460

Distance approx 9.46 km from Taconic

10

Country Victorian Serenity in the Berkshires

Berkshires / New Marlborough

New Marlborough house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Suitable for children age 5+
  • Private garden

Price per night from

$264

Price per night from

$264

Distance approx 8.5 km from Taconic Show on Map

36

Spacious Berkshires Home w/ Pool & Patio!

Berkshires / North Egremont

North Egremont house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$862

Responds fast!
avg. 7 minutes

Price per night from

$862

Distance approx 18.97 km from Taconic

(37) Excellent 

20

Berkshire Farmhouse Vacation

Berkshires / West Stockbridge

West Stockbridge house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Pet Friendly
  • Private garden
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l
…see more

Price per night from

$299

Price per night from

$299

Distance approx 9.06 km from Taconic Show on Map

15

S. Berkshires Mountain Treehouse • Views • Privacy

Berkshires / Great Barrington

Great Barrington house

2 4 14 nights min

  • 2 bedrooms
  • sleeps 4
  • 14 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$214

Responds fast!
avg. 1 hour 39 minutes

Price per night from

$214

Distance approx 18.38 km from Taconic

(1) Excellent 

14

Casa Campagna

New York / Rhinebeck

Rhinebeck house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 8 mi
  • Child Friendly
  • Air conditioning

Price per night from

$288

Price per night from

$288

Distance approx 11.37 km from Taconic

12

The FarmHouse

New York / Millerton

Millerton house

2 5 120 nights min

  • 2 bedrooms
  • sleeps 5
  • 120 nights min

Price per night from

$107

Price per night from

$107

Distance approx 9.01 km from Taconic

35

Charming Private Guest Suite in Historic Village in the Berkshires

Berkshires / New Marlborough

New Marlborough studio

Studio 2 1 night min

  • Studio
  • sleeps 2
  • 1 night min

Price per night from

$110

Price per night from

$110

Distance approx 11.45 km from Taconic

13

Quiet Country Contemporary Home on 5 Private Acres

Connecticut / West Cornwall

West Cornwall house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 6 mi
  • Child Friendly
  • Air conditioning

Price per night from

$466

Price per night from

$466

Distance approx 12.22 km from Taconic

(1) Very Good 

4

Cozy Copake Lake Cottage

New York / Copake

Copake house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Ask about pets

Price per night from

$123

Price per night from

$123

Distance approx 18.78 km from Taconic

4

Iris Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$173

Price per night from

$173

Distance approx 15.98 km from Taconic

12

Colebrook Dream

Connecticut / Colebrook

Colebrook house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$345

Price per night from

$345

Distance approx 13.97 km from Taconic

(6) Excellent 

12

The Smith Farm Homestead

Berkshires / Alford

Alford b and b

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
“Visit Great Barrington, but stay in a true New England town. Cho” Set back in the Berkshires, Alford Ma is a stone's throw from New York State. The small town borders Great Barrington, which is rich in activity. Many famous americans have roamed Bar
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Price per night from

$167

Responds fast!
avg. 3 hours 57 minutes

Price per night from

$167

Distance approx 10.51 km from Taconic

21

Private Berkshire Estate w/Pool & Tennis Court

Berkshires / Great Barrington

Great Barrington house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$661

Price per night from

$661

Distance approx 12.85 km from Taconic

10

The Barn at Copake Lake

New York / Craryville

Craryville barn

3 14 2 nights min

  • 3 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly

Price per night from

$689

Price per night from

$689

Distance approx 3.73 km from Taconic Show on Map

12

Cottage on East Twin Lakes, Internet Access, A/C.

Connecticut / Salisbury

Salisbury cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$181

Price per night from

$181

Distance approx 9.51 km from Taconic

17

Picturesque 19th century home on 3 private acres

Berkshires / New Marlborough

New Marlborough house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$173

Price per night from

$173

Distance approx 18.09 km from Taconic

(1) Average 

15

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Berkshires / Tyringham

Tyringham villa

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly

Price per night from

$454

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$454

Distance approx 14.44 km from Taconic

18

3 Bedroom Hudson Valley Farm House

New York / Craryville

Craryville guest house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$368

Price per night from

$368

Distance approx 10.48 km from Taconic

(3) Very Good 

22

Comfortable Rustic Cottage on 4 Wooded Acres with Brook

Connecticut / West Cornwall

West Cornwall cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 12 mi
  • Child Friendly
  • Air conditioning

Price per night from

$173

Price per night from

$173

Distance approx 16.11 km from Taconic

(1) Excellent 

20

Newly Renovated Colonial on the River! Sleeps 5-6

Berkshires / Stockbridge

Stockbridge house

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$328

Price per night from

$328