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.

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Guest favorite

Guesthouse in Hudson

5.0 out of 5 average rating, 47 reviews

Stylish, New Carriage House on Warren St!

Enjoy your stay at this adorable, newly-renovated, 2- bedroom Carriage House located in the heart of Hudson. Restaurants, galleries, antiques shops and bar are just steps away! This Carriage House is a free-standing 2-story, located on Warren Street. It offers a parking pass directly behind building in a municipal parking lot. The Amtrak station is a 12-15 minute walk away. The Carriage is located behind the main building which houses a gift shop and a wine bar, Sisters Hudson and Bar Bene.

Nov 8 – 15

G$78,917 GYD per night

Guest favorite

Guesthouse in Germantown

4.94 out of 5 average rating, 310 reviews

The Studio at Pear Farm

Sophisticated large studio has gorgeous light and Catskill Mountain Views Formally an artist studio, it has undergone an elegant renovation. The luxurious bathroom features premium tile and a glass walled shower The kitchen is new, nicely equipped and has a full sized refrigerator. Enjoy outdoor grilling and dining on the private deck. The studio is located on 65 pristine acres fronting directly on the Hudson River. 5 minutes to Germantown. 10 minutes to Tivoli, Hudson or Bard College.

Oct 10 – 17

G$35,502 GYD per night

Guest favorite

Guesthouse in Great Barrington

4.97 out of 5 average rating, 90 reviews

Studio in Bucolic Berkshire Setting

The 600 Sq. Ft Studio with skylights has a sitting area with sofa-bed, flat screen TV/DVD, sleep area with queen-size bed, dining area, fully equipped kitchen and full bath with shower. Views overlook a 30 acre farm (south) and mountains (east). The studio is in a separate building with a private entrance. The 4 acre property includes perennial and vegetable gardens, an orchard and walking paths. The studio is easily accessible to biking, hiking, swimming, and numerous cultural attractions.

Oct 4 – 11

G$28,731 GYD per night

Guest favorite

Guesthouse in Germantown

4.97 out of 5 average rating, 178 reviews

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 21 – 28

G$50,000 GYD per night

Guest favorite

Guesthouse in Valatie

4.95 out of 5 average rating, 55 reviews

Hudson Berkshire Lake Log Cabin

The Hudson Berkshire Martin VB Log Cabin This cute historic cabin was the Martin Van Buren hunting lodge back in the day. The cabin has been completely restored - maintaining the the vibe of the old while incorporating modern The cabin has an open kitchen with separate dining area and living room - facing an old stone fireplace. There is separate bedroom and bathroom. The log cabin has a private open-field backyard surrounded by trees - ideal idea breakfast, lunch or even a barbecue.

Jul 9 – 16

G$49,914 GYD per night

Guest favorite

Guesthouse in Great Barrington

4.96 out of 5 average rating, 50 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Jun 1 – 8

G$38,412 GYD per night

Superhost

Guesthouse in Hillsdale

4.82 out of 5 average rating, 89 reviews

Cozy Cottage with Mountain Views

Come have a peaceful and cozy stay with mountain views in the quaint town of Hillsdale! Steps from the Harlem Valley Rail Trail, and minutes from hiking, water falls, and nature abound. The cottage is situated in the perfect location where the Hudson Valley meets the Berkshires and is a great spot to check out all the nearby towns - from the posh town of Hudson, NY to Great Barrington, MA. Incredible culture, restaurants, shops, glorious landscapes and beautiful views await you!

Jul 15 – 22

G$31,772 GYD per night

Guest favorite

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.

Jun 22 – 29

G$26,119 GYD per night

Guest favorite

Guesthouse in Germantown

4.99 out of 5 average rating, 137 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).

Dec 15 – 22

G$29,314 GYD per night

Guest favorite

Guesthouse in Hudson

5.0 out of 5 average rating, 26 reviews

Hudson Countryside Guest Cottage w/Amazing Views

Relax and unwind at this unique and tranquil getaway. This private guest cottage offers stunning views of the Catskill Mountain and heart-shaped pond. Explore the property, visit with the horses and lounge near the pond. The perfect location for the perfect getaway! Conveniently located central to Hudson, Catskill and Germantown (5 miles to each), where you can enjoy amazing restaurants, antique shops, art galleries and entertainment.

Sep 17 – 24

G$54,938 GYD per night

Guest favorite

Guesthouse in Hudson

5.0 out of 5 average rating, 17 reviews

Serene one bedroom guest house with fireplace.

Serene 900 square foot guest cottage located eight miles from Hudson, City center. The guest house is located near the main house and has a private entrance and partially screened-off stone patio—Sunny, bright, cheerful interior with king-size bed. The bathroom has a shower, heated floors, and a washer and dryer. The kitchen has a microwave, refrigerator, coffee maker, toaster, and electric tea kettle.

Mar 20 – 27

G$54,300 GYD per night

Guest favorite

Guesthouse in Hillsdale

4.8 out of 5 average rating, 5 reviews

Hudson valley and The Berkshires Cottage

Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, stylish 1 bedroom cottage; perfect for a couple or a solo vacationer looking for solitude. We believe you’re here to completely relax, that’s why we have no requirements when checking out, just turn the lights off and lock the door!

Jul 12 – 19

G$38,869 GYD per night