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175 Houses

(4) Excellent 

10

Great Vacation House in the Berkshires on Richmond Pond

Berkshires / Richmond

Richmond house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$214

Price per night from

$214

12

Idyllic Berkshire Home perfect for families or friends with pool and gardens

Berkshires / Richmond

Richmond house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child Friendly

Price per night from

$573

Price per night from

$573

20

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

Berkshires / Richmond

Richmond house

3 6 7 nights min

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

Price per night from

$573

Price per night from

$573

Great rentals within 20 miles that match your search

Distance approx 8.81 km from Richmond

29

Beauty in the Berkshires

New York / Austerlitz

Austerlitz house

6 14 2 nights min

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

Price per night from

$1,379

Price per night from

$1,379

Distance approx 9.2 km from Richmond

31

Big Beautiful 7 bedroom 3 bath hot tub pool table

Berkshires / Pittsfield

Pittsfield house

7 18 2 nights min

  • 7 bedrooms
  • sleeps 18
  • 2 nights min
  • Child Friendly
  • Ask about pets

Price per night from

$345

Price per night from

$345

Distance approx 9.66 km from Richmond

(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 16.47 km from Richmond

32

Berkshire Home on Lake Garfield w/Dock & Boats

Berkshires / Monterey

Monterey house

4 12 min stay varies

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

Price per night from

$345

Responds fast!
avg. 7 minutes

Price per night from

$345

Distance approx 19.87 km from Richmond

(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 16.73 km from Richmond

13

Designer Loft Style Residence

Berkshires / Sheffield

Sheffield house

3 6 7 nights min

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

Price per night from

$517

Price per night from

$517

Distance approx 7.04 km from Richmond

(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 11.48 km from Richmond

(24) Excellent 

18

Berkshires: Romantic Cottage with spectacular view

Berkshires / Great Barrington

Great Barrington cottage

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything loo
…see more

Price per night from

$259

Price per night from

$259

Distance approx 9.02 km from Richmond

18

Mountain Views Atop Blueberry Hill on 40 Acres

New York / Austerlitz

Austerlitz house

3 6 2 nights min

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

Price per night from

$230

Price per night from

$230

Distance approx 17.88 km from Richmond

8

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Berkshires / Hinsdale

Hinsdale house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Ask about pets
  • Private garden

Price per night from

$167

Price per night from

$167

Distance approx 4.52 km from Richmond Show on Map

24

NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

Berkshires / Lenox

Lenox house

3 6 3 nights min

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

Price per night from

$431

Responds fast!
avg. 36 minutes

Price per night from

$431

Distance approx 3.62 km from Richmond Show on Map

(2) Excellent 

8

Cozy & Modern Home -mins from Tanglewood & Kripalu

Berkshires / West Stockbridge

West Stockbridge apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Ask about children
  • Air conditioning
  • Ask about pets

Price per night from

$115

Responds fast!
avg. 2 hours 34 minutes

Price per night from

$115

Distance approx 15.08 km from Richmond

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 18.17 km from Richmond

(13) Very Good 

13

Quiet Comfortable Cabin 5 Min. Walk to Lake

Berkshires / Becket

Becket house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets
“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
…see more

Price per night from

$172

Price per night from

$172

Distance approx 18.19 km from Richmond

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

$263

Price per night from

$263

Distance approx 7.36 km from Richmond

(2) Very Good 

12

Berkshires Spacious Comfortable Charming Farmhouse

Berkshires / Lee

Lee apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
…see more

Price per night from

$345

Responds fast!
avg. 1 hour 42 minutes

Price per night from

$345

Distance approx 19.41 km from Richmond

16

Roaring Rapids Cottage

New York / Columbiaville

Columbiaville house

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 3 mi
  • Ask about children
  • Air conditioning

Price per night from

$288

Price per night from

$288

Distance approx 15.98 km from Richmond

6

Berkshires on the Pond

Berkshires / Becket

Becket house

2 2 4 nights min

  • 2 bedrooms
  • sleeps 2
  • 4 nights min
  • Nearest beach 16 mi
  • Ask about children
  • Private garden

Price per night from

$144

Price per night from

$144

Distance approx 11.29 km from Richmond

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 16.84 km from Richmond

19

Relaxing Victorian Farmhouse

New York / Philmont

Philmont house

3 4 2 nights min

  • 3 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$224

Price per night from

$224

Distance approx 6.29 km from Richmond

(1) Excellent 

34

INTERIOR DESIGNERS BOTANICAL GARDENS

Berkshires / Lenox

Lenox cottage

1 5 min stay varies

  • 1 bedroom
  • sleeps 5
  • min stay varies
  • Nearest beach 3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$121

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$121

Distance approx 13.73 km from Richmond

12

Fabulous Post & Beam Berkshire Rental

Berkshires / Monterey

Monterey house

7 21 nights min

  • sleeps 7
  • 21 nights min
  • Ask about children
  • Car not necessary
  • Ask about pets

Price per night from

$206

Price per night from

$206

Distance approx 9.58 km from Richmond

6

Stunning Home! 120 Acres! Amazing!

Berkshires / Great Barrington

Great Barrington house

9 16 3 nights min

  • 9 bedrooms
  • sleeps 16
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$4,135

Price per night from

$4,135

Distance approx 13.37 km from Richmond

7

Berkshires Cottage Country Retreat

New York / Stephentown

Stephentown cottage

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Private garden

Price per night from

$189

Responds fast!
avg. 2 hours 19 minutes

Price per night from

$189

Distance approx 10.79 km from Richmond

(6) Excellent 

23

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

New York / Stephentown

Stephentown lodge

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$431

Responds fast!
avg. 1 hour 50 minutes

Price per night from

$431

Distance approx 4.47 km from Richmond Show on Map

23

Renovated 2 bedroom in Heart of Lenox

Berkshires / Lenox

Lenox apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$345

Price per night from

$345

Distance approx 5.06 km from Richmond

4

Horse Room

Berkshires / Stockbridge

Stockbridge farmhouse

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$173

Price per night from

$173

Distance approx 12.02 km from Richmond

19

Berkshire Country Estate - Rose Suite

New York / Old Chatham

Old Chatham villa

2 4 2 nights min

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

Price per night from

$196

Price per night from

$196

Distance approx 15.19 km from Richmond

(3) Very Good 

25

Stunning New Construction All SeasonLakefront Home

New York / Valatie

Valatie house

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning
“Fantastic House -- Lake, Poor” Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our opinion. It's murky-black. We did go s
…see more

Price per night from

$279

Price per night from

$279

Distance approx 14.55 km from Richmond

10

Red Mapple Farm

New York / Malden Bridge

Malden Bridge house

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Ski
  • Child Friendly

Price per night from

$506

Price per night from

$506

Distance approx 12.94 km from Richmond

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 13.74 km from Richmond

10

Vacation Village in the Berkshires Available July 22-29

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$181

Price per night from

$181

Distance approx 13.18 km from Richmond

(2) Very Good 

16

Berkshires Vacation Rental - Bentley Brook Resort Suite

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$229

Price per night from

$229

Distance approx 13.29 km from Richmond

8

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$230

Price per night from

$230

Distance approx 6.37 km from Richmond

31

|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|

Berkshires / Stockbridge

Stockbridge house

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$517

Responds fast!
avg. 1 hour 31 minutes

Price per night from

$517