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106 Houses

(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

Great rentals within 20 miles that match your search

Distance approx 19.82 km from Hawley

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

$344

Price per night from

$344

Distance approx 12.68 km from Hawley

(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 14.04 km from Hawley

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

$166

Price per night from

$166

Distance approx 7.15 km from Hawley

(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.
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Price per night from

$149

Price per night from

$149

Distance approx 19.41 km from Hawley

14

Christmas in The Berkshires

Berkshires / Hancock

Hancock condo

1 4 2 nights min

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

Price per night from

$258

Price per night from

$258

Distance approx 19.77 km from Hawley

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

$212

Responds fast!
avg. 24 minutes

Price per night from

$212

Distance approx 15.59 km from Hawley

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. 7 minutes

Price per night from

$344

Distance approx 8.6 km from Hawley

(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.
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Price per night from

$573

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$573

Distance approx 14.32 km from Hawley

(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

$327

Price per night from

$327

Distance approx 4.12 km from Hawley

(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 10.93 km from Hawley

(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 16.52 km from Hawley

(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.
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Price per night from

$178

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$178

Distance approx 18.73 km from Hawley

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 18.88 km from Hawley

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 16.98 km from Hawley

17

House On Main Street

Berkshires / Williamstown

Williamstown house

4 16 2 nights min

  • 4 bedrooms
  • sleeps 16
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$573

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$573

Distance approx 12.72 km from Hawley

11

OWL'S NEST LODGING

Massachusetts / Conway

Conway apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Ski
  • Suitable for children age 5+

Price per night from

$189

Price per night from

$189

Distance approx 19.37 km from Hawley

(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

$115

Price per night from

$115

Distance approx 12.57 km from Hawley

(4) Excellent 

16

Lakefront Summer Vacation Cottages

Hampshire County / Goshen

Goshen cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$195

Price per night from

$195

Distance approx 9.27 km from Hawley

(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
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Price per night from

$172

Price per night from

$172

Distance approx 18.7 km from Hawley

24

Vacation Village in the Berkshires

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

$180

Price per night from

$180

Distance approx 18.8 km from Hawley

24

Wilmington Home w/Pool Access- 20 Mins to Mt. Snow

Vermont / Wilmington

Wilmington house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$189

Responds fast!
avg. 7 minutes

Price per night from

$189

Distance approx 19.44 km from Hawley

(1) Very Good 

23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Berkshires / Hancock

Hancock condo

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$228

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$228

Distance approx 19.41 km from Hawley

(1) Very Good 

13

Mount Snow Area Home with 5 Bedrooms

Vermont / Wilmington

Wilmington house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$344

Price per night from

$344

Distance approx 12.25 km from Hawley

26

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

Massachusetts / Shelburne Falls

Shelburne Falls studio

Studio 6 min stay varies

  • Studio
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$189

Responds fast!
avg. 7 minutes

Price per night from

$189

Distance approx 19.54 km from Hawley

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

$514

Price per night from

$514

Distance approx 16.39 km from Hawley

18

Penthouse at Brandt House B&B

Massachusetts / Greenfield

Greenfield b and b

1 4 2 nights min

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

Price per night from

$286

Price per night from

$286

Distance approx 10.62 km from Hawley

38

Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

Berkshires / Adams

Adams house

7 14 2 nights min

  • 7 bedrooms
  • sleeps 14
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$458

Price per night from

$458

Distance approx 12.28 km from Hawley

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

$81

Price per night from

$81

Distance approx 12.7 km from Hawley

14

ROOM walking distance to Mass MoCa

Berkshires / North Adams

North Adams apartment

1 8 min stay varies

  • 1 bedroom
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$115

Price per night from

$115

Distance approx 19.15 km from Hawley

(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

$2,862

Price per night from

$2,862

Distance approx 17.04 km from Hawley

9

Cozy farmhouse, walk to campus & town

Berkshires / Williamstown

Williamstown house

2 5 2 nights min

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

Price per night from

$361

Price per night from

$361

Distance approx 19.41 km from Hawley

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

$180

Price per night from

$180

Distance approx 19.76 km from Hawley

(1) Very Good 

6

Jiminy Peak Ski Resort-Country Village's Best Unit

Berkshires / Hancock

Hancock apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly

Price per night from

$287

Responds fast!
avg. 7 minutes

Price per night from

$287

Distance approx 13.71 km from Hawley

19

Charming Berkshires lakefront house, great views

Berkshires / Cheshire

Cheshire house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Car not necessary

Price per night from

$229

Price per night from

$229

Distance approx 17.5 km from Hawley

25

NEW! Family Home w/Game Room - 3 Mi to Jiminy Peak

Berkshires / Hancock

Hancock house

4 20 min stay varies

  • 4 bedrooms
  • sleeps 20
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$287

Responds fast!
avg. 7 minutes

Price per night from

$287

Distance approx 19.44 km from Hawley

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

$229

Price per night from

$229

Distance approx 10.99 km from Hawley

10

Sweet Berkshire Getaway

Berkshires / North Adams

North Adams house

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Nearest beach 0.5 mi
  • Private garden

Price per night from

$224

Price per night from

$224