Holiday rentals in Tyringham

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Top-rated holiday rentals in Tyringham

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

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)

13–20 Sep

€ 143 per night
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

€ 384 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

€ 294 per night

Popular amenities for Tyringham holiday rentals

Stay near Tyringham's top sights

Tyringham Cobble Park19 locals recommend
Ashintully Gardens13 locals recommend
Santarella6 locals recommend

Other great holiday rentals in Tyringham

Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 101 reviews

Private 2nd-floor studio on a working produce farm

26 Jul – 2 Aug

€ 159 per night
Guest favourite

Guest house in Lenox

4.94 out of 5 average rating, 271 reviews

The Granary at House on Golden Hill

6–13 Jun

€ 213 per night
Superhost

Home in Becket

4.93 out of 5 average rating, 114 reviews

Lake front retreat - Stylish Berkshire home

6–13 Aug

€ 809 per night
Guest favourite

Cottage in Great Barrington

4.98 out of 5 average rating, 124 reviews

Newly built cottage on working farm

7–14 Nov

€ 121 per night
Guest favourite

Cabin in Lee

4.9 out of 5 average rating, 102 reviews

Cozy cabin with panoramic views in the Berkshires

10–17 Sep

€ 433 per night
Guest favourite

Guest suite in Canaan

4.98 out of 5 average rating, 290 reviews

Walk to Brewery in Historic Railroad Depot

29 Nov – 6 Dec

€ 148 per night
Guest favourite

Home in Lee

5.0 out of 5 average rating, 33 reviews

GreenHouse

1–8 Sep

€ 157 per night
Guest favourite

Home in Tyringham

4.84 out of 5 average rating, 64 reviews

Treetop Hideaway in Tyringham

13–20 Jun

€ 432 per night
Guest favourite

Home in Becket

4.94 out of 5 average rating, 36 reviews

Nerd Preservation Sanctuary

21–28 Oct

€ 99 per night
Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 42 reviews

Sweet 1-bedroom with salt water pool

11–18 May

€ 162 per night
Guest favourite

Home in Otis

4.82 out of 5 average rating, 56 reviews

Wintertime Oasis in the Berkshires

23–30 Jun

€ 137 per night
Guest favourite

Home in Monterey

4.9 out of 5 average rating, 39 reviews

- Lake Front 4 Bdr w/ Fast Internet! -

8–15 Sep

€ 488 per night

Destinations to explore