Photo by Elizabeth Massa Peroulakis

Search Condo Rentals in Middlefield

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 31 Condo Rentals in Middlefield with updated reviews, rates, and availability.

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 704
SAR 810 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Exterior

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

10.0 out of 10, Exceptional, (6)
"We love Jiminy Peak and having a week at a ski-in, ski-out unit was fantastic. We skied back for lunch and skied back out for the afternoon; skied in for a quick dinner and the boys skied back out for night skiing. Terrific location! Kitchen was clean and serviceable (no oven but two burners, sink, dishwasher, microwave, and toaster) and beds were good. Everything was easy... check in, check out, so smooth. A great time was had by all!!!!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Snow and ski sports

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

10.0 out of 10, Exceptional, (28)
"Had an amazing stay here! Place was exactly like the photos. Fireplace was perfect! Great places to hike around the area. Host was great with fast communication. "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Snow and ski sports

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

10.0 out of 10, Exceptional, (36)
"This was a perfect home base for our family vacation in the Berkshires. Centrally located, clean, had everything we needed, and the pool access was a huge plus with the kids! "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Living area

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

9.4 out of 10, Exceptional, (17)
"We had a great time here. I just didn’t realize there was no oven and the stove top only had 2 burners. My bad as I didn’t read close enough. Still had a blast there."
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Property grounds

Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!

10.0 out of 10, Exceptional, (1)
"I really enjoyed my stay at this Vrbo. Everything was well stocked (bedroom/bathroom/kitchen linens, cleaning supplies, kitchen appliances / serveware etc). The futon pulled out was comfortable. The flat is in a great location that is walking-distance to cafes/restaurants. Tre was an excellent host!"
Cozy nest of a condo tiny home in Downtown Northampton-- walk to Smith College!
Berkshires Getaway < 1 Mi Skiing & Hiking!
Charlemont Vacation Rental | 3BR | 1.5BA | 1,800 Sq Ft | 2 Steps to Enter

Berkshires Getaway < 1 Mi Skiing & Hiking!

10.0 out of 10, Exceptional, (10)
"Beautiful spot, great location right at the mountain! We had such a great time here!"
Berkshires Getaway < 1 Mi Skiing & Hiking!
UNIQUE - 1BR Country Condo @ Jiminy Peak
Room

UNIQUE - 1BR Country Condo @ Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Friendly respnsive owner. Nice suite. Was very good for my wife, my son and I. Resort is big skiing location. Was somewhat quiet in the summer though "
UNIQUE - 1BR Country Condo @ Jiminy Peak
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Property grounds

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

9.8 out of 10, Exceptional, (10)
"Very nice condo "
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Ski on ski off 1 Br loft condo in the village center with private gated parking
Snow and ski sports

Ski on ski off 1 Br loft condo in the village center with private gated parking

10.0 out of 10, Exceptional, (13)
"My friends and I were looking for a close escape from Albany, NY. When we entered the condo we immediately felt a sense of ease and once the wood burning fire was started we were in heaven. The condo is in the perfect location within the JP Village. We were able to walk to the Country Store, Bars and Restaurants. What was PERFECT was the close proximity to the lifts; right out the door. We could ski on, ski off and take breaks without dealing with the crowds in the food halls. The condo itself...
Ski on ski off 1 Br loft condo in the village center with private gated parking
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

10.0 out of 10, Exceptional, (9)
"Love the ski in and out of this property. Family enjoyed staying here, highly recommended."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Perfect for Winter Skiing!!
Exterior

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

8.0 out of 10, Very Good, (1)
"Andrew was great and very communicative about some issues the property was having due to a burst pipe leak. He was super responsive."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
Property grounds

IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES

10.0 out of 10, Exceptional, (3)
"Our family all met at Jiminy Peak and stayed in this wonderful condo. It was as exactly as advertised, a true ski in & ski out at the base of the mountain. Check in was easy and we were very happy with this beautiful, clean and convenient condo. We had someone sleeping on the pull out couch, finding the sheets was very easy and he said it was comfortable!!! We had a great weekend and plan to stay here again next year!!!"
IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

10.0 out of 10, Exceptional, (4)
"The room and location were great! The owner was extremely helpful and responsive. We had a great time!"
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

8.6 out of 10, Excellent, (4)
"Ski trip"
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bentley_20Brook_20CW_20EX_20019_S.jpg

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Ski Jiminy Peak Xmas Wk: Fri-Mon 12/27-30 for 3 Nites; @Wyndham Bentley Brook
Exterior

Ski Jiminy Peak Xmas Wk: Fri-Mon 12/27-30 for 3 Nites; @Wyndham Bentley Brook

Ski Jiminy Peak Xmas Wk: Fri-Mon 12/27-30 for 3 Nites; @Wyndham Bentley Brook
Cozy Condo with resort amenities
Exterior with private lake

Cozy Condo with resort amenities

Cozy Condo with resort amenities
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.
Don't see what you're looking for?
See all available properties in Middlefield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middlefield

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is SAR 704
SAR 810 total
includes taxes & fees
1 Jan - 2 January 2025
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is SAR 710
SAR 778 total
includes taxes & fees
1 Jan - 2 January 2025
Jiminy Peak Mountain Resort
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.8 out of 10, Exceptional, (38)
"We had a wonderful stay. The cabin was clean and comfortable! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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.

Frequently asked questions

Why book your condo in Middlefield with Expedia?
With Expedia, it’s a cinch to find your ideal condo in Middlefield. On the lookout for a luxury escape? Use our handy filters to search for properties that are 5-star rated. If you have a certain budget, select how much you want to spend and then check out our amazing options. We’ll help you find the perfect pad whatever your getaway looks like.
How can I find cheap condos in Middlefield?
An excellent way to compare cheap condos in Middlefield is with Expedia’s filter tool. Narrow your search results by amenities, budget and star rating to land excellent rates with only a few clicks.