Guesthouse vacation rentals in Columbia County
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Top-rated guesthouse rentals in Columbia County
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Columbia County guesthouse rentals
Family-friendly guest house rentals
Guesthouse in Germantown
4.97 out of 5 average rating, 67 reviewsThe Guest House
Aug 31 – Sep 7
Guesthouse in Pine Plains
4.97 out of 5 average rating, 76 reviewsCozy Cottage by the Pond
Aug 8 – 15
Guesthouse in Germantown
4.98 out of 5 average rating, 57 reviewsThe White Barn: A Bright Barn Loft in the Country
Dec 9 – 16
Guesthouse in Germantown
4.71 out of 5 average rating, 48 reviewsQuaint Rural Cottage Immersed in Nature
Jan 20 – 27
Guesthouse in Hudson
4.99 out of 5 average rating, 75 reviewsCozy cottage on Angus Farm, 15 mins from Hudson.
Jun 22 – 29
Guest house rentals with a patio
Guesthouse in Great Barrington
4.82 out of 5 average rating, 44 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
Jun 8 – 15
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Sep 24 – Oct 1
Guesthouse in Sheffield
5.0 out of 5 average rating, 3 reviewsThe Cottage at 3 Sisters Farm
Oct 10 – 17
Guesthouse in Ghent
The Hidden Pool House
Aug 29 – Sep 3
Guesthouse in New Lebanon
Cascades Premium King A
Jun 25 – Jul 2
Guesthouse in New Lebanon
Cascades Premium King B
Dec 19 – 26
Guesthouse in New Lebanon
Cascades Queen A
Aug 21 – 28
Guesthouse in New Lebanon
Cascades Super Premium King
Nov 24 – Dec 1
Guest house rentals with a washer and dryer
Guesthouse in Red Hook
4.93 out of 5 average rating, 75 reviewsPrivate Cottage, Walk to Restaurants and Shops
Jan 18 – 25
Guesthouse in Chatham
5.0 out of 5 average rating, 7 reviewsIdyllic and cozy guesthouse
Jan 10 – 17
Guesthouse in Chatham
4.97 out of 5 average rating, 29 reviewsRestorative retreat- cozy Hudson Valley getaway
Jul 18 – 25
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Jan 1 – 8
Guesthouse in Great Barrington
4.82 out of 5 average rating, 44 reviews1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
Jun 8 – 15
Guesthouse in Chatham
4.71 out of 5 average rating, 7 reviewsTranquil Guest House, Chatham NY
May 29 – Jun 5
Guesthouse in Great Barrington
4.96 out of 5 average rating, 49 reviewsSweet Victorian in Housatonic
Jun 9 – 16
Guesthouse in Hudson
5.0 out of 5 average rating, 26 reviewsHudson Countryside Guest Cottage w/Amazing Views
Jul 24 – 31
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