Guesthouse vacation rentals in Columbia County

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Top-rated guesthouses in Columbia County

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

Guest favourite
Guesthouse in Germantown
Loblolly Cottage
Loblolly Cottage is a peaceful retreat set among towering pines on our property in Germantown NY. This guest suite harkens back to an authentic 1930s Adirondack cabin that features a reclaimed barn wood interior with vaulted ceilings and antique beams. Outside enjoy our fantastic deck with a Cabana kitchen and fire pit. A short stroll will lead you to the heart of the hamlet where you will find an array of shops and restaurants. Loblolly Cottage is a unique one-of-a-kind vacation experience.
Jun. 30 – Jul. 7
$304 CAD per night
4.97 out of 5 average rating, 176 reviews
Guest favourite
Guesthouse in Germantown
Luxe Guest House Retreat
Welcome to the Guest House nestled in the woods. We designed this lush and light-filled studio with peace and luxury in mind. Situated across from apple orchards, it sits ten minutes from Hudson and ten minutes from Germantown, you get the best of both worlds: country living with two amazing destinations close by. Ideal for a romantic getaway, or to be close to the sights and sounds but can retreat to natural beauty. A true sanctuary from the City.
Jul. 31 – Aug. 7
$190 CAD per night
4.96 out of 5 average rating, 185 reviews
Guest favourite
Guesthouse in Germantown
The Loft
This beautiful loft apartment is located in the heart of Germantown- just 0.3 miles from Otto's Market (groceries and deli), 3 minute walk to Gaskins Restaurant, "A charming eatery serving a locally-sourced menu of classic American fare in a rustic dining room." We offer tea & coffee in the loft, parking, yard access, wifi, basic amenities, full kitchen and a smart TV that has a fire stick with access to Amazon Prime and Netflix (no cable).
Sep. 6 – 13
$180 CAD per night
5.0 out of 5 average rating, 125 reviews

Popular amenities for Columbia County guesthouses

Family-friendly guesthouses

Guest favourite
Guesthouse in Germantown
The Guest House
May 23 – 30
$421 CAD per night
4.97 out of 5 average rating, 67 reviews
Guesthouse in Germantown
Quaint Rural Cottage Immersed in Nature
Feb. 13 – 20
$217 CAD per night
4.71 out of 5 average rating, 48 reviews
Guest favourite
Guesthouse in Pine Plains
Cozy Cottage by the Pond
Mar. 9 – 16
$222 CAD per night
4.97 out of 5 average rating, 76 reviews
Guest favourite
Guesthouse in Germantown
The White Barn: A Bright Barn Loft in the Country
Oct. 9 – 16
$342 CAD per night
4.98 out of 5 average rating, 57 reviews
Guest favourite
Guesthouse in Hudson
Cozy cottage on Angus Farm, 15 mins from Hudson.
Apr. 25 – May 2
$403 CAD per night
4.99 out of 5 average rating, 71 reviews

Guesthouses with a patio

Guest favourite
Guesthouse in Great Barrington
Sweet Victorian in Housatonic
May 29 – Jun. 5
$401 CAD per night
5.0 out of 5 average rating, 38 reviews
Guest favourite
Guesthouse in Valatie
Hudson Berkshire Lake Log Cabin
Oct. 2 – 9
$347 CAD per night
4.94 out of 5 average rating, 54 reviews
Superhost
Guesthouse in Great Barrington
1-bed unit 3/4 mi. from GB dwntwn. EV friendly.
Apr. 30 – May 7
$306 CAD per night
4.82 out of 5 average rating, 44 reviews
Guest favourite
Guesthouse in Hudson
Serene one bedroom guest house with fireplace.
Oct. 12 – 19
$382 CAD per night
5.0 out of 5 average rating, 17 reviews
Guest favourite
Guesthouse in Hudson
Stylish, New Carriage House on Warren St!
Jan. 3 – 10
$512 CAD per night
5.0 out of 5 average rating, 42 reviews
Guest favourite
Guesthouse in Hudson
Hudson Countryside Guest Cottage w/Amazing Views
Dec. 3 – 10
$371 CAD per night
5.0 out of 5 average rating, 26 reviews
Superhost
Guesthouse in Austerlitz
The Recording Studio @ Moonbeams
Mar. 24 – 31
$840 CAD per night
New place to stay
Guest favourite
Guesthouse in Salisbury
Guest House with spectacular views
Jun. 17 – 22
$526 CAD per night
5.0 out of 5 average rating, 5 reviews
Guesthouse in Sheffield
The Cottage at 3 Sisters Farm
Mar. 19 – 26
$384 CAD per night
New place to stay
Guesthouse in Ghent
The Hidden Pool House
Oct. 6 – 11
$386 CAD per night
New place to stay
Guesthouse in New Lebanon
Cascades Queen A
Jun. 11 – 18
$209 CAD per night
New place to stay
Guesthouse in New Lebanon
Cascades Premium King A
May 1 – 8
$240 CAD per night
New place to stay

Guesthouse rentals with a washer and dryer

Superhost
Guesthouse in Chatham
Tranquil Guest House, Chatham NY
Apr. 20 – 27
$336 CAD per night
4.71 out of 5 average rating, 7 reviews
Guest favourite
Guesthouse in Red Hook
Private Cottage, Walk to Restaurants and Shops
Nov. 14 – 21
$365 CAD per night
4.93 out of 5 average rating, 75 reviews
Guest favourite
Guesthouse in Great Barrington
Renovated Private Guest House by Evergreen Home
Oct. 1 – 8
$463 CAD per night
4.94 out of 5 average rating, 16 reviews
Guest favourite
Guesthouse in Chatham
Idyllic and cozy guesthouse
Mar. 15 – 22
$235 CAD per night
5.0 out of 5 average rating, 5 reviews
Guest favourite
Guesthouse in Chatham
Restorative retreat- cozy Hudson Valley getaway
May 16 – 23
$496 CAD per night
4.97 out of 5 average rating, 29 reviews

Destinations to explore