Middlefield Ski Chalets
Cottage
10.0(47 Reviews)
3 Bedrooms
1 Bath
4 Guests
650 ft²
Ocean View
Balcony/Terrace
View
Kitchen
CA $334/Night
7 Nights - CA $2,336
House
3 Bedrooms
2 Baths
6 Guests
3056.95 ft²
Fireplace/Heating
Pet Friendly
Parking
Air Conditioner
CA $364/Night
7 Nights - CA $2,547
House
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
Internet
Child Friendly
Barbecue/Outdoor Cooking
Security/Safety
CA $105/Night
7 Nights - CA $736
House
10.0(193 Reviews)
3 Bedrooms
2 Baths
6 Guests
1650 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $370/Night
7 Nights - CA $2,590
House
10.0(92 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $403/Night
7 Nights - CA $2,820
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
7 Guests
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $590/Night
7 Nights - CA $4,126
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
2700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $552/Night
7 Nights - CA $3,862
Cottage
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
CA $353/Night
7 Nights - CA $2,471
House
9.8(22 Reviews)
3 Bedrooms
2 Baths
6 Guests
3055 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $475/Night
7 Nights - CA $3,324
House
9.6(25 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $403/Night
7 Nights - CA $2,820
House
9.6(9 Reviews)
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $739/Night
7 Nights - CA $5,175
House
8.6(4 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Security/Safety
CA $491/Night
7 Nights - CA $3,439
Why Choose Rent By Owner for your Middlefield Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Middlefield
How to Book Your Middlefield Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Middlefield
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Middlefield, MA
Skyline Trail
Frequently Asked Questions About Middlefield Rental Ski Chalets
1. What are the top Ski Chalets in Middlefield?
There are a lot of options in Middlefield. If you plan on staying in the Middlefield area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Middlefield:
- Berkshires Log Cabin by Evergreen Home
- A-Frame in Sherwood Forest
- HavenHaus: Cozy A-Frame Cabin in the Berkshires
- Shingle style, Timber Frame, Berkshire Cottage beside babbling brook
- Cozy Cottage in the Woods -- near all Berkshire attractions
- Staycation at Private lake cottage near Jacob’s Pillow and Tanglewood
- Berkshire Mountain Retreat near Jacobs Pillow
- Tranquil Washington Home w/ Sauna, on 70 Acres
- Bershire Home Rental: Enjoy Berkshire Fall Foliage
- Historic 1804 house in N Becket Village in the Berkshires
2. How many Ski Chalets are available in Middlefield?
Currently, the total number of properties listed by RBO in 2026 is over 37 in the Middlefield area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Middlefield.
More Rentals You May Like Near Middlefield
Cabin
4 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Internet
- Child Friendly
Laundry
CA $773/Night
7 Nights - CA $5,410
Cabin
3 Bedrooms
2 Baths
8 Guests
2700 ft²
- Hot Tub
Spa- Fireplace/Heating
Pool
CA $256/Night
7 Nights - CA $1,792
House
10.0(5 Reviews)
4 Bedrooms
3 Baths
10 Guests
3300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $1,151/Night
7 Nights - CA $8,060
House
9.8(58 Reviews)
4 Bedrooms
2 Baths
8 Guests
1400 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
CA $634/Night
7 Nights - CA $4,439
House
7 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $2,377/Night
7 Nights - CA $16,637
New
Cottage
3 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
CA $529/Night
7 Nights - CA $3,703
Other
10.0(23 Reviews)
3 Bedrooms
2 Baths
4 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
CA $314/Night
7 Nights - CA $2,199
Other
9.4(70 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
CA $309/Night
7 Nights - CA $2,167
House
10.0(19 Reviews)
2 Bedrooms
1 Bath
6 Guests
1170 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
CA $632/Night
7 Nights - CA $4,425
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
7 Guests
- Spa
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $468/Night
7 Nights - CA $3,279
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
6 Guests
2000 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
CA $221/Night
7 Nights - CA $1,546
House
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
CA $250/Night
7 Nights - CA $1,748
