Cottage vacation rentals in Columbia County

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Top-rated cottage rentals in Columbia County

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

Guest favourite
Cottage in Catskill
1930's Cottage unique charm near skiing
1 bedroom 1930's guest cottage with a full living room. Near 3 skiing areas. Window air conditioner brand new, ceiling fans in living room and bedroom. Separate windowed bedroom with new full size mattress. Full size gas stove, microwave, fridge, Keurig coffee maker, toaster and large tiled counter and sink. Full bath off bedroom with large clawfoot tub and shower combination and sink and brand new toilet. Wifi , flat screen Smart TV. Vintage cast iron fireplace with electric insert.
Sep. 13 – 20
$141 CAD per night
4.96 out of 5 average rating, 225 reviews
Guest favourite
Cottage in Kinderhook
The Cottage on Sylvester Street
The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.
Jun. 18 – 25
$205 CAD per night
4.98 out of 5 average rating, 164 reviews
Guest favourite
Cottage in New Lebanon
The Writer's Cottage
The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.
Oct. 14 – 21
$170 CAD per night
4.94 out of 5 average rating, 173 reviews

Popular amenities for Columbia County cottage rentals

Cottage rentals with a hot tub

Guest favourite
Cottage in Red Hook
Goose Landing Cottage by the lake with NEW Hot Tub
Dec. 27 – Jan. 3
$352 CAD per night
4.92 out of 5 average rating, 318 reviews
Guest favourite
Cottage in Ravena
Pet Friendly • Fenced Yard • Hot Tub • Romantic
Apr. 16 – 23
$289 CAD per night
4.74 out of 5 average rating, 141 reviews
Cottage in Hudson
Private hot tub + Remodeled Cottage
Mar. 12 – 19
$253 CAD per night
4.81 out of 5 average rating, 63 reviews
Superhost
Cottage in Red Hook
Lakefront cottage-year round hot tub -The Lily Pad
Jan. 14 – 21
$470 CAD per night
4.85 out of 5 average rating, 122 reviews
Superhost
Cottage in Red Hook
LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE
May 4 – 11
$430 CAD per night
4.9 out of 5 average rating, 190 reviews

Pet-friendly cottage rentals

Guest favourite
Cottage in Red Hook
bright serene + spacious barn
Nov. 7 – 14
$468 CAD per night
4.98 out of 5 average rating, 586 reviews
Guest favourite
Cottage in Hillsdale
Cozy Cottage Catamount, Berkshires Walk to Brewery
Aug. 16 – 23
$207 CAD per night
4.94 out of 5 average rating, 168 reviews
Guest favourite
Cottage in Catskill
Charming Cottage in the Heart of Catskill
Jun. 30 – Jul. 7
$267 CAD per night
4.98 out of 5 average rating, 133 reviews
Guest favourite
Cottage in Hudson
Historic Hudson Cottage
Apr. 12 – 19
$218 CAD per night
4.88 out of 5 average rating, 150 reviews
Superhost
Cottage in Hudson
Peaceful waterfront getaway near Hudson, NY
May 11 – 18
$215 CAD per night
4.84 out of 5 average rating, 112 reviews
Guest favourite
Cottage in Ancram
Warmer Temps & Special Rates-Now Is the Time To Go
Feb. 2 – 9
$322 CAD per night
4.99 out of 5 average rating, 165 reviews
Guest favourite
Cottage in Old Chatham
Berkshires / Hudson Loft
Jun. 6 – 13
$225 CAD per night
4.8 out of 5 average rating, 163 reviews
Guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
Jun. 15 – 22
$268 CAD per night
5.0 out of 5 average rating, 132 reviews
Guest favourite
Cottage in Chatham Center
Kinderhook Creek Private Retreat
Apr. 26 – May 3
$361 CAD per night
4.89 out of 5 average rating, 148 reviews
Superhost
Cottage in Canaan
Plan your Berkshires by the lake
Apr. 1 – 8
$322 CAD per night
4.9 out of 5 average rating, 125 reviews
Superhost
Cottage in Catskill
Rustic Chic Carriage House near nature & Hudson
Jan. 31 – Feb. 7
$135 CAD per night
4.74 out of 5 average rating, 68 reviews
Guest favourite
Cottage in Catskill
Cozy Creative 2BR Cottage in the Heart of Catskill
Mar. 30 – Apr. 6
$182 CAD per night
4.9 out of 5 average rating, 70 reviews

Private cottage rentals

Guest favourite
Cottage in Hillsdale
Big Bliss Near Catamount Cottage w/Modern Flair
Nov. 30 – Dec. 7
$230 CAD per night
4.83 out of 5 average rating, 235 reviews
Guest favourite
Cottage in Copake Falls
Beautiful cottage in Copake Falls
May 16 – 23
$231 CAD per night
4.9 out of 5 average rating, 312 reviews
Guest favourite
Cottage in Valatie
Kinderhook Lake cottage-private+kayaks/sup+swim+ac
Nov. 9 – 16
$407 CAD per night
4.99 out of 5 average rating, 127 reviews
Guest favourite
Cottage in Stuyvesant
Perfect Cottage On A Hill With A View
Jul. 26 – Aug. 2
$313 CAD per night
4.93 out of 5 average rating, 138 reviews
Guest favourite
Cottage in Red Hook
CoZy Newly Renovated Cottage in Red Hook Village
Aug. 17 – 24
$335 CAD per night
4.98 out of 5 average rating, 207 reviews
Guest favourite
Cottage in West Stockbridge
Historic 1810 Farmhouse - Fully Renovated
Apr. 26 – May 3
$394 CAD per night
4.98 out of 5 average rating, 104 reviews
Guest favourite
Cottage in Great Barrington
Newly built cottage on working farm
Apr. 9 – 16
$178 CAD per night
4.98 out of 5 average rating, 123 reviews
Guest favourite
Cottage in Tivoli
Clausterhaus
Jan. 30 – Feb. 4
$351 CAD per night
4.96 out of 5 average rating, 193 reviews
Superhost
Cottage in Hudson
The Hudson Hideaway_EST 2017
May 31 – Jun. 7
$377 CAD per night
4.82 out of 5 average rating, 109 reviews
Guest favourite
Cottage in Kinderhook
Spacious Cottage Retreat on Beautiful 2-Acres
Jan. 13 – 20
$156 CAD per night
4.96 out of 5 average rating, 74 reviews
Guest favourite
Cottage in Niverville
Huge Lakefront, Cozy Private Cottage in Upstate NY
Sep. 18 – 25
$413 CAD per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Cottage in Catskill
Cozy Catskill Cottage
Aug. 16 – 23
$267 CAD per night
4.98 out of 5 average rating, 43 reviews

Destinations to explore