Holiday rentals in Readsboro

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Top-rated holiday rentals in Readsboro

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

Guest favourite

Flat in Wilmington

4.88 out of 5 average rating, 277 reviews

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

14–21 Aug

£111 per night
Superhost

Home in Readsboro

4.86 out of 5 average rating, 118 reviews

Vermont March Madness! (Pet Friendly)

Quiet, clean, home, well stocked, exclusively yours, nestled in Green Mtns with prime access on a flat road, babbling brook. Great location! Winter activities, antiques, shops, lakes, hike, covered bridges, cozy dinner at local inns by a fireplace, mountain views! Enjoy Vermont! Scenic roads, Prospect Mt. or Mt. Snow, VAST trails, hiking, Mt.Greylock, Mass MOCA, in nearby N.Adams, MA, (12 min)Berkshires w/in an hour. 20 mins to Bennington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

14–21 Sept

£88 per night
Guest favourite

Tiny home in Wilmington

4.98 out of 5 average rating, 128 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

11–18 Sept

£189 per night

Popular amenities for Readsboro holiday rentals

Other great holiday rentals in Readsboro

Guest favourite

Flat in Wilmington

4.93 out of 5 average rating, 189 reviews

Studio Apartment Sleeps 4,

11–18 Oct

£112 per night
Guest favourite

Guest suite in Brattleboro

4.94 out of 5 average rating, 515 reviews

Charming studio in renovated 19th century church.

24 Nov – 1 Dec

£87 per night
Guest favourite

Guest house in North Adams

4.92 out of 5 average rating, 177 reviews

"Worker's" Cottage (circa 1860).

7–14 May

£115 per night
Guest favourite

Guest suite in Charlemont

4.9 out of 5 average rating, 180 reviews

Unique People & Pet-Welcoming Haven

14–21 Aug

£107 per night
Guest favourite

Guest house in Brattleboro

4.93 out of 5 average rating, 421 reviews

Mahalo Temple Retreat

5–12 May

£83 per night
Guest favourite

Guest house in North Bennington

4.98 out of 5 average rating, 143 reviews

Birch House - lake, green trees + modern comforts

17–24 Aug

£139 per night
Guest favourite

Cabin in Savoy

4.98 out of 5 average rating, 184 reviews

The Camp - 20 Minutes to Berkshire East!

25 Aug – 1 Sept

£103 per night
Guest favourite

Flat in Greenfield

4.96 out of 5 average rating, 257 reviews

Mohawk Trail View/ private apt. no cleaning Fee

23–30 Jul

£93 per night
Guest favourite

Tiny home in Brattleboro

4.95 out of 5 average rating, 173 reviews

"Mountain View" Hike In Cabin Retreat

24–31 Aug

£84 per night
Guest favourite

Flat in North Adams

4.95 out of 5 average rating, 711 reviews

Guest Apt. Near MCLA & MASS MoCA

27 Dec – 3 Jan

£100 per night
Guest favourite

Guest suite in Greenfield

4.94 out of 5 average rating, 143 reviews

Pristine Oasis with Private Bath

10–17 Nov

£65 per night
Guest favourite

Cabin in Readsboro

4.93 out of 5 average rating, 68 reviews

The Hidden Gem

31 Aug – 7 Sept

£163 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Readsboro