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Middlefield Holiday Rentals

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences

Holiday Rental House
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Craftsman Home In The Berkshire Forest

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshires Private Large Lakefront Home On Robin Hood Lake

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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A-Frame in Sherwood Forest

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Elegant Wilderness Cabin 12 Miles From Northampton

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serene, Private Waterfront House --Perfect Summer Retreat!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spacious waterfront Berkshire home family private get-away

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful four season lakeside log home close to all Berkshires attractions.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Remote and Relaxing Cabin in the Berkshires

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bershire Home Rental: Enjoy Berkshire Fall Foliage

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Modern Secluded Home In Wooded Setting

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peace And Quiet On The Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshire Lake access

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage In The Berkshires In Western Massachusetts

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming cedar shingle cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beautiful Timber Frame Home in the Berkshires /Available for Long Term

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Scenic ByWay Waterfront Property

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Shingle style, Timber Frame, Berkshire Cottage beside babbling brook

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Berkshires Lake Retreat, Beautifully Updated with Mid-Century Style

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Lakefront Home in Berkshires

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Berkshire Cottage on Ashmere Lake

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Picturesque Cottage with Sunroom on Ashmere Lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Berkshires Vacation Home on Hayden Pond

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming Cabin Lake Rights, Private Dock 3 bedroom, 2 bath

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Berkshire custom luxury home in private wooded community- walk to lake

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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NEW Secluded A-Frame Cabin: Fire Pit, Walk to Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Staycation at Private lake cottage near Jacob’s Pillow and Tanglewood

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Escape to the Berkshires!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet Comfortable Cabin 5 Min. Walk to Lake

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire 4Br Cape Cottage near Big Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Deluxe New Home, 2 Master Suites, Tanglewood Area

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Tamarack at Running Fox Berry Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Farmhouse surrounded by beautiful fall foliage!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Heart of Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake house in the heart of the Berkshires

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Huntington Home - Walk to Westfield River

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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