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.

Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

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

11–18 Sep

$506 SGD per night
Guest favourite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy 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

$169 SGD per night
Guest favourite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 reviews

Gingerbread 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

$384 SGD per night

Popular amenities for Middlefield holiday rentals

Other great holiday rentals in Middlefield

Guest favourite

Guest house in Northampton

5.0 out of 5 average rating, 271 reviews

Mill River Cottage (pet friendly!)

5–12 Dec

$163 SGD per night
Guest favourite

Flat in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

14–21 Sep

$144 SGD per night
Guest favourite

Flat in Greenfield

4.96 out of 5 average rating, 258 reviews

Mohawk Trail View/ private apt. no cleaning Fee

23–30 Jul

$141 SGD per night
Guest favourite

Cabin in Becket

5.0 out of 5 average rating, 254 reviews

Waldtreff - quiet grand cabin

30 May – 6 Jun

$343 SGD per night
Guest favourite

Flat in Leeds

4.99 out of 5 average rating, 114 reviews

Private Studio for a Sweet Getaway!

6–13 Apr

$162 SGD per night
Guest favourite

Home in New Lebanon

4.99 out of 5 average rating, 347 reviews

The old sawmill from 1771

24–31 Jul

$194 SGD per night
Guest favourite

Home in Lee

5.0 out of 5 average rating, 225 reviews

Berkshire Mountain retreat with Urban eco-luxuries

19–26 Mar

$440 SGD per night
Guest favourite

Farm stay in Worthington

5.0 out of 5 average rating, 9 reviews

Like sleeping on a cloud

1–8 Nov

$232 SGD per night
Guest favourite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

21–28 Oct

$127 SGD per night
Guest favourite

Home in Chester

4.97 out of 5 average rating, 39 reviews

Halloween Decorated Turn of Century Family Home

25 Aug – 1 Sep

$151 SGD per night
Guest favourite

Campervan/Motorhome in Westhampton

4.88 out of 5 average rating, 80 reviews

AirbytheStream waterfront, private, clean and cozy

22–29 Sep

$121 SGD per night
Guest favourite

Home in Becket

4.92 out of 5 average rating, 12 reviews

Forest Home with Sauna

18–25 Jun

$312 SGD per night

Destinations to explore