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Chesterfield Holiday Rentals

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50 rentals in Chesterfield.
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Elegant Wilderness Cabin 12 Miles From Northampton, holiday rental in Chesterfield

Elegant Wilderness Cabin 12 Miles From Northampton

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

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Big farmhouse in the foothills of the Berkshires, holiday rental in Chesterfield

Big farmhouse in the foothills of the Berkshires

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Unique People & Pet-Welcoming Country Haven, holiday rental in Chesterfield

Unique People & Pet-Welcoming Country Haven

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, holiday rental in Chesterfield

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

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 Chesterfield

Waterfront Home on Pine Island Lake

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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A-Frame in Sherwood Forest, holiday rental in Chesterfield

A-Frame in Sherwood Forest

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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In town, newly remodeled studio with private balcony, holiday rental in Chesterfield

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 Chesterfield

Modern Rustic House Overlooking The Deerfield River

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful four season lakeside log home close to all Berkshires attractions., holiday rental in Chesterfield

Beautiful four season lakeside log home close to all Berkshires attractions.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, holiday rental in Chesterfield

Spacious waterfront Berkshire home family private get-away

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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1810 Brook Side Mill/House / Winter Fun Getaway in Western MA, holiday rental in Chesterfield

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

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

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

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

Charming New England House Surrounded By Trees, Field And Pond

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Peace And Quiet On The Lake, holiday rental in Chesterfield

Peace And Quiet On The Lake

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

Remote and Relaxing Cabin in the Berkshires

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

Lakefront Cottage In The Berkshires In Western Massachusetts

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Scenic ByWay Waterfront Property, holiday rental in Chesterfield

Scenic ByWay Waterfront Property

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Charming Rural Cottage in the Heart of the Scenic Mohawk Trail, holiday rental in Chesterfield

Charming Rural Cottage in the Heart of the Scenic Mohawk Trail

2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming cedar shingle cottage, holiday rental in Chesterfield

Charming cedar shingle cottage

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, holiday rental in Chesterfield

Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Charming Affordable  Home for groups up to 14, holiday rental in Chesterfield

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 Chesterfield

Retreat in the Woods

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire house w/ fireplace, A/C, WiFi & laundry, holiday rental in Chesterfield

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

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Flight's End-A Country Home with Babbling Brook, holiday rental in Chesterfield

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 Chesterfield

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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Escape to the Berkshires!, holiday rental in Chesterfield

Escape to the Berkshires!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet Comfortable Cabin 5 Min. Walk to Lake, holiday rental in Chesterfield

Quiet Comfortable Cabin 5 Min. Walk to Lake

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 Chesterfield

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 Chesterfield

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

4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Berkshire 4Br Cape Cottage near Big Pond, holiday rental in Chesterfield

Berkshire 4Br Cape Cottage near Big Pond

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy home, secluded sledding, snowshoe trails,babbling brook,waterfalls,23 acres, holiday rental in Chesterfield

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Enjoy horses and the largest recreational lake in Massachusetts, holiday rental in Chesterfield

Enjoy horses and the largest recreational lake in Massachusetts

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,, holiday rental in Chesterfield

Etinde House is located ten minutes from Umass, Amherst College, Hampshire mall,

7 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, holiday rental in Chesterfield

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 Chesterfield

OWL'S NEST LODGING

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

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 Chesterfield

Starlight Llama - The Pink Room

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Huntington Home - Walk to Westfield River, holiday rental in Chesterfield

Historic Huntington Home - Walk to Westfield River

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!, holiday rental in Chesterfield

Serene Shelburne Studio Cabin w/Spring-Fed Pool!

0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!, holiday rental in Chesterfield

Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Picturesque Cottage with Sunroom on Ashmere Lake!, holiday rental in Chesterfield

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 Chesterfield

Tentrr Backcountry Site - Camp Cozie Nook

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Rural Berkshires Home, holiday rental in Chesterfield

Rural Berkshires Home

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake, holiday rental in Chesterfield

NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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‘Front Row’ Apt w/ Dock - Walk to Otis Reservoir!, holiday rental in Chesterfield

‘Front Row’ Apt w/ Dock - Walk to Otis Reservoir!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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‘Stargazer’ in Berkshires: Walk to Otis Reservoir!, holiday rental in Chesterfield

‘Stargazer’ in Berkshires: Walk to Otis Reservoir!

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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‘The Cozy’ Apartment in Otis - Shared Dock & Grill, holiday rental in Chesterfield

‘The Cozy’ Apartment in Otis - Shared Dock & Grill

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake house in the heart of the Berkshires, holiday rental in Chesterfield

Lake house in the heart of the Berkshires

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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