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Middlefield Vacation Rentals

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50 rentals in Middlefield.
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Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, vacation rental in Middlefield
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, vacation rental in Middlefield
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow, vacation rental in Middlefield

Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, vacation rental in Middlefield
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, vacation rental in Middlefield
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences, vacation rental in Middlefield

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, vacation rental in Middlefield
COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, vacation rental in Middlefield
COUPLE(S) PERFECT!! 2 BED/BATHS ; CENTRAL AC; FIREPL; ROMANTIC 'SKI LODGE' FEEL, vacation rental in Middlefield

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Craftsman Home In The Berkshire Forest, vacation rental in Middlefield
Craftsman Home In The Berkshire Forest, vacation rental in Middlefield
Craftsman Home In The Berkshire Forest, vacation rental in Middlefield

Craftsman Home In The Berkshire Forest

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshires  Private Large Lakefront Home On Robin Hood Lake, vacation rental in Middlefield
Berkshires  Private Large Lakefront Home On Robin Hood Lake, vacation rental in Middlefield
Berkshires  Private Large Lakefront Home On Robin Hood Lake, vacation rental in Middlefield

Berkshires Private Large Lakefront Home On Robin Hood Lake

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!, vacation rental in Middlefield
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!, vacation rental in Middlefield
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!, vacation rental in Middlefield

Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A-Frame in Sherwood Forest, vacation rental in Middlefield
A-Frame in Sherwood Forest, vacation rental in Middlefield
A-Frame in Sherwood Forest, vacation rental in Middlefield

A-Frame in Sherwood Forest

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Elegant Wilderness Cabin 12 Miles From Northampton, vacation rental in Middlefield
Elegant Wilderness Cabin 12 Miles From Northampton, vacation rental in Middlefield
Elegant Wilderness Cabin 12 Miles From Northampton, vacation rental in Middlefield

Elegant Wilderness Cabin 12 Miles From Northampton

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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PRIVATE LAKEFRONT BEACH PROPERTY ON GOOSE POND near TANGLEWOOD

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Woodland Cottage-NEW! Convenient, private, family friendly- see CLEANING DETAILS

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serene, Private Waterfront House --Perfect Summer Retreat!, vacation rental in Middlefield
Serene, Private Waterfront House --Perfect Summer Retreat!, vacation rental in Middlefield
Serene, Private Waterfront House --Perfect Summer Retreat!, vacation rental in Middlefield

Serene, Private Waterfront House --Perfect Summer Retreat!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away, vacation rental in Middlefield
Spacious waterfront Berkshire home family private get-away, vacation rental in Middlefield
Spacious waterfront Berkshire home family private get-away, vacation rental in Middlefield

Spacious waterfront Berkshire home family private get-away

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires, vacation rental in Middlefield
Remote and Relaxing Cabin in the Berkshires, vacation rental in Middlefield
Remote and Relaxing Cabin in the Berkshires, vacation rental in Middlefield

Remote and Relaxing Cabin in the Berkshires

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful four season lakeside log home close to all Berkshires attractions., vacation rental in Middlefield
Beautiful four season lakeside log home close to all Berkshires attractions., vacation rental in Middlefield
Beautiful four season lakeside log home close to all Berkshires attractions., vacation rental in Middlefield

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bershire Home Rental:  Enjoy Berkshire Fall Foliage, vacation rental in Middlefield
Bershire Home Rental:  Enjoy Berkshire Fall Foliage, vacation rental in Middlefield
Bershire Home Rental:  Enjoy Berkshire Fall Foliage, vacation rental in Middlefield

Bershire Home Rental: Enjoy Berkshire Fall Foliage

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Berkshire Cottage on Ashmere Lake, vacation rental in Middlefield
Berkshire Cottage on Ashmere Lake, vacation rental in Middlefield
Berkshire Cottage on Ashmere Lake, vacation rental in Middlefield

Berkshire Cottage on Ashmere Lake

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Peace And Quiet On The Lake, vacation rental in Middlefield
Peace And Quiet On The Lake, vacation rental in Middlefield
Peace And Quiet On The Lake, vacation rental in Middlefield

Peace And Quiet On The Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Berkshire Lake access, vacation rental in Middlefield
Berkshire Lake access, vacation rental in Middlefield
Berkshire Lake access, vacation rental in Middlefield

Berkshire Lake access

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating, vacation rental in Middlefield
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating, vacation rental in Middlefield
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating, vacation rental in Middlefield

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!, vacation rental in Middlefield
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!, vacation rental in Middlefield
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!, vacation rental in Middlefield

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lakefront Cottage In The Berkshires In Western Massachusetts, vacation rental in Middlefield
Lakefront Cottage In The Berkshires In Western Massachusetts, vacation rental in Middlefield
Lakefront Cottage In The Berkshires In Western Massachusetts, vacation rental in Middlefield

Lakefront Cottage In The Berkshires In Western Massachusetts

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming cedar shingle cottage, vacation rental in Middlefield
Charming cedar shingle cottage, vacation rental in Middlefield
Charming cedar shingle cottage, vacation rental in Middlefield

Charming cedar shingle cottage

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Beautiful Timber Frame Home in the Berkshires   /Available for Long Term, vacation rental in Middlefield
Beautiful Timber Frame Home in the Berkshires   /Available for Long Term, vacation rental in Middlefield
Beautiful Timber Frame Home in the Berkshires   /Available for Long Term, vacation rental in Middlefield

Beautiful Timber Frame Home in the Berkshires /Available for Long Term

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Scenic ByWay Waterfront Property

Rental Home
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
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Shingle style, Timber Frame,  Berkshire Cottage beside babbling brook, vacation rental in Middlefield
Shingle style, Timber Frame,  Berkshire Cottage beside babbling brook, vacation rental in Middlefield
Shingle style, Timber Frame,  Berkshire Cottage beside babbling brook, vacation rental in Middlefield

Shingle style, Timber Frame, Berkshire Cottage beside babbling brook

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, vacation rental in Middlefield
Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, vacation rental in Middlefield
Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style, vacation rental in Middlefield

Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style

Rental Home
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
More info
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Lakefront Home in Berkshires, vacation rental in Middlefield
Lakefront Home in Berkshires, vacation rental in Middlefield
Lakefront Home in Berkshires, vacation rental in Middlefield

Lakefront Home in Berkshires

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More, vacation rental in Middlefield
Lovely Lakefront Cottage, Peaceful Setting, Hiking And More, vacation rental in Middlefield
Lovely Lakefront Cottage, Peaceful Setting, Hiking And More, vacation rental in Middlefield

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, vacation rental in Middlefield
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, vacation rental in Middlefield
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft, vacation rental in Middlefield

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Ashmere Lakefront  Apartment, vacation rental in Middlefield
Ashmere Lakefront  Apartment, vacation rental in Middlefield
Ashmere Lakefront  Apartment, vacation rental in Middlefield

Ashmere Lakefront Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Ashmere Lake Log Cabin with privacy / 2 Bedrooms, vacation rental in Middlefield
Ashmere Lake Log Cabin with privacy / 2 Bedrooms, vacation rental in Middlefield
Ashmere Lake Log Cabin with privacy / 2 Bedrooms, vacation rental in Middlefield

Ashmere Lake Log Cabin with privacy / 2 Bedrooms

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming Farmhouse surrounded by beautiful fall foliage!, vacation rental in Middlefield
Charming Farmhouse surrounded by beautiful fall foliage!, vacation rental in Middlefield
Charming Farmhouse surrounded by beautiful fall foliage!, vacation rental in Middlefield

Charming Farmhouse surrounded by beautiful fall foliage!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Picturesque Cottage with Sunroom on Ashmere Lake!, vacation rental in Middlefield
Picturesque Cottage with Sunroom on Ashmere Lake!, vacation rental in Middlefield
Picturesque Cottage with Sunroom on Ashmere Lake!, vacation rental in Middlefield

Picturesque Cottage with Sunroom on Ashmere Lake!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Berkshires Vacation Home on Hayden Pond, vacation rental in Middlefield
Berkshires Vacation Home on Hayden Pond, vacation rental in Middlefield
Berkshires Vacation Home on Hayden Pond, vacation rental in Middlefield

Berkshires Vacation Home on Hayden Pond

Rental Home
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, vacation rental in Middlefield
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, vacation rental in Middlefield
Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath, vacation rental in Middlefield

Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stunning Berkshire custom luxury home in private wooded community- walk to lake, vacation rental in Middlefield
Stunning Berkshire custom luxury home in private wooded community- walk to lake, vacation rental in Middlefield
Stunning Berkshire custom luxury home in private wooded community- walk to lake, vacation rental in Middlefield

Stunning Berkshire custom luxury home in private wooded community- walk to lake

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake, vacation rental in Middlefield
NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake, vacation rental in Middlefield
NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake, vacation rental in Middlefield

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Staycation at Private lake cottage near Jacob’s Pillow and Tanglewood, vacation rental in Middlefield
Staycation at Private lake cottage near Jacob’s Pillow and Tanglewood, vacation rental in Middlefield
Staycation at Private lake cottage near Jacob’s Pillow and Tanglewood, vacation rental in Middlefield

Staycation at Private lake cottage near Jacob’s Pillow and Tanglewood

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Escape to the Berkshires!, vacation rental in Middlefield
Escape to the Berkshires!, vacation rental in Middlefield
Escape to the Berkshires!, vacation rental in Middlefield

Escape to the Berkshires!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Quiet Comfortable Cabin 5 Min. Walk to Lake, vacation rental in Middlefield
Quiet Comfortable Cabin 5 Min. Walk to Lake, vacation rental in Middlefield
Quiet Comfortable Cabin 5 Min. Walk to Lake, vacation rental in Middlefield

Quiet Comfortable Cabin 5 Min. Walk to Lake

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Berkshire 4Br Cape Cottage near Big Pond, vacation rental in Middlefield
Berkshire 4Br Cape Cottage near Big Pond, vacation rental in Middlefield
Berkshire 4Br Cape Cottage near Big Pond, vacation rental in Middlefield

Berkshire 4Br Cape Cottage near Big Pond

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Deluxe New Home, 2 Master Suites, Tanglewood Area, vacation rental in Middlefield
Deluxe New Home, 2 Master Suites, Tanglewood Area, vacation rental in Middlefield
Deluxe New Home, 2 Master Suites, Tanglewood Area, vacation rental in Middlefield

Deluxe New Home, 2 Master Suites, Tanglewood Area

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts, vacation rental in Middlefield
New Timberframe House Rental in the Berkshire Mountains, Masschusetts, vacation rental in Middlefield
New Timberframe House Rental in the Berkshire Mountains, Masschusetts, vacation rental in Middlefield

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Tentrr Signature Site - Tamarack at Running Fox Berry Farm, vacation rental in Middlefield
Tentrr Signature Site - Tamarack at Running Fox Berry Farm, vacation rental in Middlefield
Tentrr Signature Site - Tamarack at Running Fox Berry Farm, vacation rental in Middlefield

Tentrr Signature Site - Tamarack at Running Fox Berry Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness, vacation rental in Middlefield
The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness, vacation rental in Middlefield
The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness, vacation rental in Middlefield

The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond, vacation rental in Middlefield
New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond, vacation rental in Middlefield
New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond, vacation rental in Middlefield

New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Heart of Berkshires, vacation rental in Middlefield
The Heart of Berkshires, vacation rental in Middlefield
The Heart of Berkshires, vacation rental in Middlefield

The Heart of Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Home in The Berkshires - Becket, vacation rental in Middlefield
Home in The Berkshires - Becket, vacation rental in Middlefield
Home in The Berkshires - Becket, vacation rental in Middlefield

Home in The Berkshires - Becket

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Lake house in the heart of the Berkshires, vacation rental in Middlefield
Lake house in the heart of the Berkshires, vacation rental in Middlefield
Lake house in the heart of the Berkshires, vacation rental in Middlefield

Lake house in the heart of the Berkshires

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Historic Huntington Home - Walk to Westfield River, vacation rental in Middlefield
Historic Huntington Home - Walk to Westfield River, vacation rental in Middlefield
Historic Huntington Home - Walk to Westfield River, vacation rental in Middlefield

Historic Huntington Home - Walk to Westfield River

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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