Holiday houses in Columbia County

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Top-rated holiday rentals in Columbia County

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Guest favourite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

14–21 Oct

$207 NZD per night

Guest favourite

Home in Catskill

4.99 out of 5 average rating, 132 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

Athens, NY Entire House - 1 bedroom Quiet Country setting Springtime - or anytime is a great time to escape to upstate NY. Guests have called it "a very cozy cottage in the woods". It is set back off the road and a great place to get away and unwind. 10 minutes from Exit 21 on the NYS Thruway and is an easy drive to several towns on the Hudson River. They are known for their restaurants, local shops and quaint downtowns. Area features outdoor activities: hiking trails, skiing and kayaking.

9–16 Jun

$269 NZD per night

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 180 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

6–13 Aug

$277 NZD per night

Guest favourite

Cottage in Kinderhook

4.98 out of 5 average rating, 171 reviews

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.

26 Sep – 3 Oct

$256 NZD per night

Guest favourite

Home in Ghent

4.96 out of 5 average rating, 213 reviews

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Grocery and bar packages are available upon request and can be set-up prior to arrival. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!

26 Feb – 5 Mar

$310 NZD per night

Guest favourite

Home in Chatham

4.9 out of 5 average rating, 144 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to fine dining & Main St pubs/pizza/movies/shopping. 12mi Hudson Amtrak (taxi, Uber avail). Walk to town park w/swim pond. 30mins Albany/Lenox. Keyless entry. Hosts a text away if needed. Smoke/Pet-free property. Check-in 4pm/-out 11a. 55" Sony Roku TV. Reliable high-speed WiFi. Stocked kitchen/full bath incl W/D. Private outdoor dining area w/propane bbq. 2 guests max preferred, a 3rd could be accommodated at extra charge.

11–18 Oct

$218 NZD per night

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 478 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking.

11–18 Dec

$235 NZD per night

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 106 reviews

Main Street Cottage

We are on a well traveled, main road. Close to everything! For nature lovers, explore the area with hikes on local trails or on a kayak down the river. Just a few minutes drive, explore the Hudson River Skywalk and the homes of Thomas Cole and Fredrick Church. Stroll down Warren Street for shopping and food. The fall brings lovely foliage and the unique taste of New York apples. The Catskills has much to offer and our cottage is in the perfect area to enjoy it all!

24 Sep – 1 Oct

$287 NZD per night

Guest favourite

Guesthouse in Germantown

4.96 out of 5 average rating, 188 reviews

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.

11–18 Aug

$237 NZD per night

Guest favourite

Guesthouse in Germantown

5.0 out of 5 average rating, 134 reviews

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).

23–30 Jan

$250 NZD per night

Guest favourite

Farm stay in Ancram

4.95 out of 5 average rating, 264 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door.

8–15 Dec

$279 NZD per night

Guest favourite

Condo in Hudson

4.94 out of 5 average rating, 140 reviews

Harmony Valley Home, bright & inviting 2-BR escape

You and your guests will be close to it all when you stay at our centrally-located home. The space is nestled perfectly between the Berkshire and Catskill Mountains, which provides countless opportunities for adventure! Whether a romantic getaway or a family vacation- you are an idea away from an unforgetable experience! Wineries breweries Musuems Hiking trails Empire State Rail Trail Conservation Areas

24 Feb – 3 Mar

$249 NZD per night