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86 Houses

6

Beautiful Vacation Home on a Private Lake

New York / Petersburg

Petersburg house

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$214

Price per night from

$214

68

The Lodge at Fox Hollow

New York / Petersburg

Petersburg house

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$260

Price per night from

$260

Great rentals within 20 miles that match your search

Distance approx 16.01 km from Petersburg

4

The Meadow House 4 bdrm 4 bath house

New York / Stephentown

Stephentown house

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$630

Price per night from

$630

Distance approx 14.17 km from Petersburg

24

Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$185

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$185

Distance approx 13.95 km from Petersburg

(3) Very Good 

14

2200sf Country House on 16 Acres-2 Miles to Jiminy

Berkshires / Hancock

Hancock house

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope
…see more

Price per night from

$225

Price per night from

$225

Distance approx 15.54 km from Petersburg

23

The Dacha: Summer/Skiing House in the Berkshires

New York / Treadwell

Treadwell apartment

2 6 3 nights min

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

Price per night from

$230

Price per night from

$230

Distance approx 19.4 km from Petersburg

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

$300

Price per night from

$300

Distance approx 7.99 km from Petersburg

17

House On Main Street

Berkshires / Williamstown

Williamstown house

4 16 min stay varies

  • 4 bedrooms
  • sleeps 16
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$500

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$500

Distance approx 12.42 km from Petersburg

(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

$175

Price per night from

$175

Distance approx 7.84 km from Petersburg

20

Karin's Place

Green Mountains / Bennington

Bennington house

7 30 2 nights min

  • 7 bedrooms
  • sleeps 30
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,350

Price per night from

$1,350

Distance approx 17.26 km from Petersburg

7

"The Barn" on Tower Mountain

Berkshires / Hancock

Hancock house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min

Price per night from

$150

Price per night from

$150

Distance approx 16.01 km from Petersburg

(17) Excellent 

10

Stone School Cottage

Berkshires / Lanesboro

Lanesboro cottage

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden
“A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.
…see more

Price per night from

$155

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$155

Distance approx 13.28 km from Petersburg

(1) Excellent 

26

Whitman Woods - A Berkshire Vacation

Berkshires / Hancock

Hancock house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Private garden

Price per night from

$101

Price per night from

$101

Distance approx 12.66 km from Petersburg

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

$185

Price per night from

$185

Distance approx 16.01 km from Petersburg

(5) Excellent 

29

Troy, NY - Timeless Rensselaer

New York / Troy

Troy apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$120

Responds fast!
avg. 1 hour 8 minutes

Price per night from

$120

Distance approx 18.84 km from Petersburg

(4) Excellent 

31

Berkshires Waterfront Lakehouse Sanctuary

Berkshires / Lanesboro

Lanesboro house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$195

Responds fast!
avg. 3 hours 29 minutes

Price per night from

$195

Distance approx 13.75 km from Petersburg

(2) Excellent 

16

PanoramicView1000 sq ft Guest Quarters Berkshires

Berkshires / Hancock

Hancock cottage

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$145

Price per night from

$145

Distance approx 15.95 km from Petersburg

28

Gorgeous Newly Renovated Victorian with an Amazing treehouse and playground

New York / Troy

Troy house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$225

Price per night from

$225

Distance approx 19.42 km from Petersburg

(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

$150

Price per night from

$150

Distance approx 19.2 km from Petersburg

24

Peaceful 5BR Nassau Duplex w/ Beautiful Lawn

New York / Nassau

Nassau house

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$112

Responds fast!
avg. 8 minutes

Price per night from

$112

Distance approx 14.16 km from Petersburg

(1) Excellent 

10

Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak

Berkshires / Hancock

Hancock hotel apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$458

Price per night from

$458

Distance approx 17.33 km from Petersburg

(1) Excellent 

13

Cozy Lakefront Cottage

Vermont / Somerset

Somerset cottage

3 6 3 nights min

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

Price per night from

$150

Price per night from

$150

Distance approx 16.01 km from Petersburg

(3) Excellent 

15

Troy, NY - Collar City Hideaway

New York / Troy

Troy apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$65

Responds fast!
avg. 1 hour 8 minutes

Price per night from

$65

Distance approx 15.62 km from Petersburg

(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

$375

Responds fast!
avg. 1 hour 29 minutes

Price per night from

$375

Distance approx 16.34 km from Petersburg

12

Olde Judge Mansion B&B

New York / Troy

Troy b and b

5 11 1 night min

  • 5 bedrooms
  • sleeps 11
  • 1 night min
  • Child Friendly

Price per night from

$95

Price per night from

$95

Distance approx 14.16 km from Petersburg

(1) Very Good 

23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Berkshires / Hancock

Hancock condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$129

Responds fast!
avg. 3 hours 30 minutes

Price per night from

$129

Distance approx 17.97 km from Petersburg

15

Little Bit of Heaven

Green Mountains / Readsboro

Readsboro house

3 6 2 nights min

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

Price per night from

$99

Responds fast!
avg. 37 minutes

Price per night from

$99

Distance approx 14.21 km from Petersburg

9

Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort

Berkshires / Hancock

Hancock condo

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$450

Price per night from

$450

Distance approx 13.53 km from Petersburg

37

Meadowhurst Farm- Queen Rm 1.6 Miles from Mass MoCA

Berkshires / Clarksburg

Clarksburg room

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Pet Friendly

Price per night from

$70

Price per night from

$70

Distance approx 16.3 km from Petersburg

26

Spring, Summer, Fall Weekend Getaway

New York / Hudson

Hudson apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$204

Price per night from

$204

Distance approx 10.96 km from Petersburg

(1) Very Good 

4

Golden Triangle in the Berkshires

Berkshires / Hancock

Hancock house

2 4 2 nights min

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

Price per night from

$2,500

Price per night from

$2,500

Distance approx 12.91 km from Petersburg

20

Romantic Waterfront Vermont Cottage

Bennington / North Bennington

North Bennington house

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$164

Price per night from

$164

Distance approx 14.16 km from Petersburg

24

Ski in Ski Out, Summer fun, Wyndham Bentley Brook

Berkshires / Hancock

Hancock condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$199

Price per night from

$199

Distance approx 14.16 km from Petersburg

20

Come and bask in the beauty of Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$107

Price per night from

$107

Distance approx 13.67 km from Petersburg

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

$157

Price per night from

$157

Distance approx 14.16 km from Petersburg

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

$200

Price per night from

$200

Distance approx 14.16 km from Petersburg

19

Enjoy the fresh mountain air at Bentley Brook!

Berkshires / Hancock

Hancock studio

Studio 4 3 nights min

  • Studio
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$84

Price per night from

$84

Distance approx 13.15 km from Petersburg

25

NEW! Lakefront Averill Park Home w/Patio, Fire Pit

New York / Averill Park

Averill Park cottage

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Air conditioning

Price per night from

$100

Responds fast!
avg. 46 minutes

Price per night from

$100