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Middlefield Vacation Rentals

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Nov 21 - Nov 23
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Nov 28 - Nov 30

Vacation Rentals in Middlefield

Property grounds
The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.

Easthampton Ma.
10.0 out of 10, Exceptional, (70)
"This was our second time staying here and we had a great time!"
United States
Andy L.
$248 nightly
The price is $277
Nov 20 - Nov 21
Total with taxes and fees
The Creation Station is a cozy place so make yourself at home.
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2137)
"Great place!"
United States
Nicole
$94 nightly
The price is $105
Nov 24 - Nov 25
Total with taxes and fees
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (985)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
$149 nightly
The price is $166
Nov 19 - Nov 20
Total with taxes and fees
Jiminy Peak Mountain Resort
Private kitchen
Home in the Woods

Home in the Woods

Russell
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
$304 nightly
The price is $321
Nov 19 - Nov 20
Total with taxes and fees
Home in the Woods
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (134)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
United States
michelle
$139 nightly
The price is $156
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Nov 19 - Nov 20
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, fireplace, printers
Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!

Whately
10.0 out of 10, Exceptional, (8)
"Thanks for a great stay"
United States
Andrea M.
$1,142 nightly
The price is $1,276
Dec 15 - Dec 16
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
Oven, stovetop, dishwasher
Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton

Northampton
10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
United States
Meghan C.
$544 nightly
The price is $608
Nov 23 - Nov 24
Total with taxes and fees
Button's Modern Luxury Walkup Downtown Northampton
Property grounds
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell
10.0 out of 10, Exceptional, (143)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
United States
Jon O.
$295 nightly
The price is $312
Nov 19 - Nov 20
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
$188 nightly
The price is $206
Nov 19 - Nov 20
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Nov 19 - Nov 20
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
$404 nightly
The price is $451
Nov 23 - Nov 24
Total with taxes and fees
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
$210 nightly
The price is $235
Nov 19 - Nov 20
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"Enjoyed our stay!!!"
United States
Fred W.
$238 nightly
The price is $265
Nov 19 - Nov 20
Total with taxes and fees
Home in Great Barrington
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
$219 nightly
The price is $245
Nov 19 - Nov 20
Total with taxes and fees
Penthouse Apartment on Park Street
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Hancock
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
$210 nightly
The price is $235
Nov 19 - Nov 20
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Indoor pool
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
$220 nightly
The price is $246
Nov 20 - Nov 21
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Property grounds
Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available

Charlemont
$352 nightly
The price is $393
Nov 19 - Nov 20
Total with taxes and fees
Riverbend Berkshire East Basecamp - 3 bedrooms available
Exterior
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock
9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
$210 nightly
The price is $235
Nov 19 - Nov 20
Total with taxes and fees
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
$313 nightly
The price is $350
Nov 19 - Nov 20
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Middlefield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Clean, comfortable facilty"
Julie 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Middlefield

Everything you need to know about Middlefield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlefield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlefield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlefield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlefield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middlefield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlefield rentals

At Expedia, we put the best Middlefield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middlefield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlefield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlefield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Middlefield?

Yes, we have vacation rentals near well known sights in Middlefield, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals in Middlefield?

Pet Friendly Riverfront Home in Great Barrington: This vacation home rental near Middlefield is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Middlefield?

While exploring the area, visit family-friendly sights like Berkshire Museum, or get outside and enjoy nature at Skyline Trail. Fox Den Wildlife Management Area and Chester Town Hall are a couple of places you'll find in the larger area.

What’s a vacation rental in Middlefield like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Middlefield. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.