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Plainfield Holiday Rentals

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50 rentals in Plainfield.
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Plainfield

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

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Unique People & Pet-Welcoming Country Haven, holiday rental in Plainfield

Unique People & Pet-Welcoming Country Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Village Carriage House, holiday rental in Plainfield

Berkshire Village Carriage House

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake, holiday rental in Plainfield

Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, holiday rental in Plainfield

COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Waterfront Home on Pine Island Lake, holiday rental in Plainfield

Waterfront Home on Pine Island Lake

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont!  Come Explore!, holiday rental in Plainfield

Ski Mt. Snow! 25 Private Acres - Almost Heaven in Rustic Vermont! Come Explore!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A-Frame in Sherwood Forest, holiday rental in Plainfield

A-Frame in Sherwood Forest

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything, holiday rental in Plainfield

A Beautiful Log Cabin In The Woods, On A Lake (Pontoosuc), Yet Near Everything

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Elegant Wilderness Cabin 12 Miles From Northampton, holiday rental in Plainfield

Elegant Wilderness Cabin 12 Miles From Northampton

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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In town, newly remodeled studio with private balcony, holiday rental in Plainfield

In town, newly remodeled studio with private balcony

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Rustic House Overlooking The Deerfield River, holiday rental in Plainfield

Modern Rustic House Overlooking The Deerfield River

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cozy renovated cabin in Williamstown, steps from hiking trails, holiday rental in Plainfield

Cozy renovated cabin in Williamstown, steps from hiking trails

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Berkshire Lake House Vacation Rental, holiday rental in Plainfield

Berkshire Lake House Vacation Rental

4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, holiday rental in Plainfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

8 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
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Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special, holiday rental in Plainfield

Historic Red Schoolhouse featured in the 2015 Home & Garden TV Special

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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1810 Brook Side Mill/House / Winter Fun Getaway in Western MA, holiday rental in Plainfield

1810 Brook Side Mill/House / Winter Fun Getaway in Western MA

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, holiday rental in Plainfield

Remote and Relaxing Cabin in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming New England House Surrounded By Trees, Field And Pond, holiday rental in Plainfield

Charming New England House Surrounded By Trees, Field And Pond

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, holiday rental in Plainfield

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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19th c. Renovated Barn in the Berkshires, holiday rental in Plainfield

19th c. Renovated Barn in the Berkshires

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A roomy remodeled retreat close to MassMoCA, holiday rental in Plainfield

A roomy remodeled retreat close to MassMoCA

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage In The Berkshires In Western Massachusetts, holiday rental in Plainfield

Lakefront Cottage In The Berkshires In Western Massachusetts

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, holiday rental in Plainfield

Charming Rural Cottage in the Heart of the Scenic Mohawk Trail

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak., holiday rental in Plainfield

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

5 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bershire Home Rental:  Enjoy Berkshire Fall Foliage, holiday rental in Plainfield

Bershire Home Rental: Enjoy Berkshire Fall Foliage

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Spring Escape, Get away in the falls❤️, holiday rental in Plainfield

Spring Escape, Get away in the falls❤️

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort, holiday rental in Plainfield

6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Ashmere Lake Log Cabin with privacy / 2 Bedrooms, holiday rental in Plainfield

Ashmere Lake Log Cabin with privacy / 2 Bedrooms

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Affordable  Home for groups up to 14, holiday rental in Plainfield

Charming Affordable Home for groups up to 14

7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Retreat in the Woods, holiday rental in Plainfield

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7, holiday rental in Plainfield

Creekside Country Comfort, Northampton Access! Lovely apartment sleeps 7

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Flight's End-A Country Home with Babbling Brook, holiday rental in Plainfield

Flight's End-A Country Home with Babbling Brook

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View, holiday rental in Plainfield

A True Shangri-La-Country Retreat W/Pond, Gardens and Huge Deck and View

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Apartment in Grand Victorian Home 1, holiday rental in Plainfield

Exquisite Apartment in Grand Victorian Home 1

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded large country home for big groups with giant open yard for outdoor fun., holiday rental in Plainfield

Secluded large country home for big groups with giant open yard for outdoor fun.

4 bedrooms
2 bathrooms
Sleeps 15
Match: Sleeps
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Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun, holiday rental in Plainfield

Stunning mountain top lodge, Ideal for groups of all kinds, 4 -season fun

6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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4 Bedroom House Close to UMass/Amherst, Historic Deerfield & Yankee Candle, holiday rental in Plainfield

4 Bedroom House Close to UMass/Amherst, Historic Deerfield & Yankee Candle

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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6BR Berkshire Bliss - 38 private acres - close to skiing and town, holiday rental in Plainfield

6BR Berkshire Bliss - 38 private acres - close to skiing and town

6 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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Mounatin Getaway in the Heart of the Berkshires!, holiday rental in Plainfield

Mounatin Getaway in the Heart of the Berkshires!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Exquisite Apartment in Grand Victorian 2, holiday rental in Plainfield

Exquisite Apartment in Grand Victorian 2

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Plainfield

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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OWL'S NEST LODGING, holiday rental in Plainfield

OWL'S NEST LODGING

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Starlight Llama - The White Room, holiday rental in Plainfield

Starlight Llama - The White Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Starlight Llama - The Pink Room, holiday rental in Plainfield

Starlight Llama - The Pink Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Bear Den, holiday rental in Plainfield

The Bear Den

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tentrr Signature Site - Hidden Hoosic   Riverside Camp, holiday rental in Plainfield

Tentrr Signature Site - Hidden Hoosic Riverside Camp

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Tamarack at Running Fox Berry Farm, holiday rental in Plainfield

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rural Berkshires Home, holiday rental in Plainfield

Rural Berkshires Home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Modern A-Frame in Southern Vermont, holiday rental in Plainfield

Beautiful Modern A-Frame in Southern Vermont

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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