Skip to content

Holiday rentals in Middlefield

Find and book unique accommodation on Airbnb

When results are available, navigate with the up and down arrow keys or explore by touch or swipe gestures.

Top-rated holiday rentals in Middlefield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
7–14 SeptIndividual Host,
£352 per night
4.94 out of 5 average rating, 341 reviews
Guest favourite
Guest house in Becket
Country Cabin
Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.
5–12 AprIndividual Host,
£109 per night
4.93 out of 5 average rating, 256 reviews
Guest favourite
Cabin in Cummington
Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.
25 Oct – 1 Nov
£59 per night
4.98 out of 5 average rating, 159 reviews

Popular amenities for Middlefield holiday rentals

Other great holiday rentals in Middlefield

Superhost
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
1–8 DecIndividual Host,
£231 per night
4.86 out of 5 average rating, 284 reviews
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
3–10 JunIndividual Host,
£274 per night
5.0 out of 5 average rating, 216 reviews
Guest favourite
Cabin in Becket
Waldtreff - quiet grand cabin
7–14 MayIndividual Host,
£242 per night
5.0 out of 5 average rating, 253 reviews
Guest favourite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
9–16 May
£296 per night
5.0 out of 5 average rating, 219 reviews
Guest favourite
Home in Rhinebeck
Architectural wonder in the woods
25 Jul – 1 AugIndividual Host,
£461 per night
4.91 out of 5 average rating, 248 reviews
Guest favourite
Home in Dalton
The Yellow House
3–10 OctIndividual Host,
£117 per night
4.91 out of 5 average rating, 111 reviews
Guest favourite
Earthen home in West Sand Lake
The Hobbit House at June Farms
4–11 FebProfessional Host,
£291 per night
4.98 out of 5 average rating, 142 reviews
Guest favourite
Flat in Plainfield
Sunny, light filled loft in 1873 Colonial
4–11 MayIndividual Host,
£108 per night
4.97 out of 5 average rating, 236 reviews
Guest favourite
Guest house in Lenox
The Granary at House on Golden Hill
8–15 MayIndividual Host,
£138 per night
4.95 out of 5 average rating, 260 reviews
Guest favourite
Guest house in Granby
Windy Top Cottage ~ A Romantic "European" Getaway
15–22 NovIndividual Host,
£152 per night
4.99 out of 5 average rating, 688 reviews
Guest favourite
Home in Becket
Lake front retreat - Stylish Berkshire home
25 Jun – 2 JulIndividual Host,
£528 per night
4.93 out of 5 average rating, 114 reviews
Guest favourite
Home in Otis
Idyllic family retreat - spacious lake home,
4–11 MayIndividual Host,
£225 per night
4.94 out of 5 average rating, 141 reviews

Destinations to explore