Holiday rentals in Middlefield
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Top-rated holiday rentals in Middlefield
Guests agree: these stays are highly rated for location, cleanliness and more.
Chalet in Otis
4.94 out of 5 average rating, 346 reviewsMid-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
11–18 Sep
Home in Lee
4.89 out of 5 average rating, 234 reviewsCozy Berkshires Cottage
Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)
8–15 May
Treehouse in Tyringham
5.0 out of 5 average rating, 222 reviewsGingerbread House Tower in the Berkshire Hills
Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.
13–20 May
Holiday rentals for every style
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Popular amenities for Middlefield holiday rentals
Other great holiday rentals in Middlefield
Guest house in Northampton
5.0 out of 5 average rating, 271 reviewsMill River Cottage (pet friendly!)
5–12 Dec
Flat in Copake Falls
4.93 out of 5 average rating, 250 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
14–21 Sep
Flat in Greenfield
4.96 out of 5 average rating, 258 reviewsMohawk Trail View/ private apt. no cleaning Fee
23–30 Jul
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
30 May – 6 Jun
Flat in Leeds
4.99 out of 5 average rating, 114 reviewsPrivate Studio for a Sweet Getaway!
6–13 Apr
Home in New Lebanon
4.99 out of 5 average rating, 347 reviewsThe old sawmill from 1771
24–31 Jul
Home in Lee
5.0 out of 5 average rating, 225 reviewsBerkshire Mountain retreat with Urban eco-luxuries
19–26 Mar
Farm stay in Worthington
5.0 out of 5 average rating, 9 reviewsLike sleeping on a cloud
1–8 Nov
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
21–28 Oct
Home in Chester
4.97 out of 5 average rating, 39 reviewsHalloween Decorated Turn of Century Family Home
25 Aug – 1 Sep
Campervan/Motorhome in Westhampton
4.88 out of 5 average rating, 80 reviewsAirbytheStream waterfront, private, clean and cozy
22–29 Sep
Home in Becket
4.92 out of 5 average rating, 12 reviewsForest Home with Sauna
18–25 Jun
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