A snow-covered forest with a stone bridge in the background.

Search Middlefield Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Middlefield cottages

A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

1. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (54 reviews)
"Great lake house in the beautiful Berkshires. House looked just like the online pics. Kitchen fully stocked with everything you would need. Lake view & backyard were amazing! Lots of fun using kayaks & canoes."
United States
Rose Angela M.
$493 nightly
The price is $551
Oct 23 - Oct 24
Total with taxes and fees
Cozy Cottage-Sunset On The Lake
A two-story house with a balcony, a chimney, and a window with a view.

2. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
$1,912 nightly
The price is $1,941
Nov 2 - Nov 3
Total with taxes and fees
Berkshires farm, 30+ guests, 50 acres
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlefield Hotel Reviews

Berkshires Untold

Berkshires Untold

8/10 Good
"Fantastic location, and friendly staff. The rooms were comfortable."
David 1-night trip
Posted less than an hour ago
Berkshires Untold

Find out more about Middlefield

Middlefield Cottages information

Number of reviews
54
Accommodation
91 Cottages
Lowest Price
$551
Highest Price
$1,941

Frequently asked questions

Why book your cottage in Middlefield with Expedia?
Expedia has some superb cottages in Middlefield, so start packing for a memorable stay on nature's doorstep. If you have a budget in mind, select how much you want to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect place whatever your trip looks like.
How can I find cheap cottages in Middlefield?
With Expedia's convenient filter tool, scoring cheap cottages in Middlefield couldn't be easier. To find accommodations that'll make your wallet smile, narrow down your search by amenities, star rating and budget.
What is there to do in Middlefield near my cottage?
The most practical travel accessory is a well-planned schedule. Skyline Trail is a top place to kick off your adventures in Middlefield.

Explore a world of travel with Expedia