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Plainfield Holiday Apartments

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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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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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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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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, holiday rental in Plainfield

Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences

3 bedrooms
2 bathrooms
Sleeps 6
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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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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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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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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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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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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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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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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Sweet Spot in a Region that Shines in Every Season, holiday rental in Plainfield

Sweet Spot in a Region that Shines in Every Season

3 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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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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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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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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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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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
More info
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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
More info
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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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Cozy home, secluded sledding, snowshoe trails,babbling brook,waterfalls,23 acres, holiday rental in Plainfield

Cozy home, secluded sledding, snowshoe trails,babbling brook,waterfalls,23 acres

3 bedrooms
2 bathrooms
Sleeps 8
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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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Plainfield

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

0 bedrooms
1 bathroom
Sleeps 6
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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Picturesque Cottage with Sunroom on Ashmere Lake!, holiday rental in Plainfield

Picturesque Cottage with Sunroom on Ashmere Lake!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Backcountry Site - Camp Cozie Nook, holiday rental in Plainfield

Tentrr Backcountry Site - Camp Cozie Nook

1 bedroom
1 bathroom
Sleeps 6
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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NEW! Lakeside Berkshires Home Near Hiking & Skiing, holiday rental in Plainfield

NEW! Lakeside Berkshires Home Near Hiking & Skiing

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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