Plainfield Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

85 Houses

(16) Very Good 

27

Berkshire house w/ fireplace, A/C, WiFi & laundry

Hampshire County / Plainfield

Plainfield house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Ski
“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.
…see more

Price per night from

$204

Responds fast!
avg. 2 hours 32 minutes

Price per night from

$204

Great rentals within 20 miles that match your search

Distance approx 18.16 km from Plainfield

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

$301

Price per night from

$301

Distance approx 19.75 km from Plainfield

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

$186

Responds fast!
avg. 10 minutes

Price per night from

$186

Distance approx 18.85 km from Plainfield

(4) Excellent 

20

Escape to the Berkshires!

Berkshires / Becket

Becket house

4 8 2 nights min

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

Price per night from

$275

Price per night from

$275

Distance approx 10.8 km from Plainfield

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

$166

Price per night from

$166

Distance approx 16.2 km from Plainfield

(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 10.51 km from Plainfield

(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

$500

Responds fast!
avg. 1 hour 28 minutes

Price per night from

$500

Distance approx 19.57 km from Plainfield

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

$226

Price per night from

$226

Distance approx 18.38 km from Plainfield

14

Riverview apt in Mill B&B near Northampton/Amherst

Hampshire County / Hatfield

Hatfield b and b

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 8.77 km from Plainfield

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

$145

Price per night from

$145

Distance approx 16.62 km from Plainfield

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

$186

Price per night from

$186

Distance approx 7.63 km from Plainfield

(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

$171

Price per night from

$171

Distance approx 11.02 km from Plainfield

18

Historic Home on 8.5 Acres

Berkshires / Dalton

Dalton house

3 9 3 nights min

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

Price per night from

$401

Price per night from

$401

Distance approx 7.34 km from Plainfield Show on Map

(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

$200

Price per night from

$200

Distance approx 18.95 km from Plainfield

(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

$105

Responds fast!
avg. 3 hours 59 minutes

Price per night from

$105

Distance approx 18.91 km from Plainfield

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

$157

Price per night from

$157

Distance approx 4.48 km from Plainfield Show on Map

(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

$150

Responds fast!
avg. 2 hours 20 minutes

Price per night from

$150

Distance approx 19.44 km from Plainfield

(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

$200

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$200

Distance approx 18.93 km from Plainfield

25

Historic Huntington Home - Walk to Westfield River

Hampshire County / Huntington

Huntington house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$191

Responds fast!
avg. 10 minutes

Price per night from

$191

Distance approx 19.61 km from Plainfield

(10) Very Good 

21

Wyndham Bentley Brook at Jiminy Peak

Berkshires / Hancock

Hancock hotel apartment

2 8 min stay varies

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

Price per night from

$251

Price per night from

$251

Distance approx 19.52 km from Plainfield

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

$451

Price per night from

$451

Distance approx 19.45 km from Plainfield

20

Fun & Relaxation Combine at 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 16.97 km from Plainfield

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

$249

Price per night from

$249

Distance approx 16.98 km from Plainfield

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 19.45 km from Plainfield

20

The ideal family fun vacation resort!

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

$108

Price per night from

$108

Distance approx 9.34 km from Plainfield

24

Rustic Goshen Cabin w/ Fire Pit, BBQ & Great Deck!

Hampshire County / Goshen

Goshen log cabin

2 8 min stay varies

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

Price per night from

$211

Responds fast!
avg. 24 minutes

Price per night from

$211

Distance approx 19.44 km from Plainfield

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 19.45 km from Plainfield

22

Come Enjoy The Beautiful Bentley Brook Resort

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$188

Price per night from

$188

Distance approx 19.45 km from Plainfield

20

Come experience the beauty that is 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 19.45 km from Plainfield

19

Enjoy cozy Bentley Brook for your family getaway!

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 15.24 km from Plainfield

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

$195

Price per night from

$195

Distance approx 19.43 km from Plainfield

67

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

Berkshires / Hancock

Hancock house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$117

Price per night from

$117

Distance approx 17.48 km from Plainfield

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

$251

Responds fast!
avg. 2 hours 57 minutes

Price per night from

$251

Distance approx 19.45 km from Plainfield

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 19.46 km from Plainfield

24

Tibet House

Hampshire County / Northampton

Northampton apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$130

Price per night from

$130

Distance approx 19.45 km from Plainfield

19

Enjoy the natural beauty of 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

$85

Price per night from

$85

Distance approx 18.51 km from Plainfield

13

new Condo close to Route 91, Northampton and Five Colleges

Hampshire County / Hatfield

Hatfield condo

3 6 2 nights min

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

Price per night from

$450

Responds fast!
avg. 3 hours 37 minutes

Price per night from

$450

Distance approx 19.45 km from Plainfield

19

Visit the nearby Hancock Shaker Village, est. 1791

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

$85

Price per night from

$85