Columbia County Holiday Rentals

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Our top choices for Columbia County holiday rentals

Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (148 reviews)
"I would absolutely stay here again. It was such a charming property that is run by lovely people. You can tell it’s run with care. Great value for the area. "
United States
Liz
The price is HK$1,018
HK$1,140 total
includes taxes & fees
8 Jun - 9 Jun
Micosta Leisure Inn
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$769
HK$1,036 total
includes taxes & fees
1 Jun - 2 Jun
All comforts of home
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is HK$832
HK$1,107 total
includes taxes & fees
2 Jun - 3 Jun
All the comforts of home
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is HK$1,175
HK$1,500 total
includes taxes & fees
31 May - 1 Jun
The Brooks Motel: Exceptional Suite
Exterior

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is HK$1,551
HK$3,545 total
includes taxes & fees
1 Jun - 2 Jun
Near Tanglewood: Historic Summer Retreat
Interior

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is HK$1,465
HK$2,843 total
includes taxes & fees
31 May - 1 Jun
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Fridge, microwave, oven, stovetop

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$1,465
HK$2,843 total
includes taxes & fees
31 May - 1 Jun
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Interior

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is HK$1,377
HK$4,245 total
includes taxes & fees
21 Jun - 22 Jun
Charles Cottage Near Warren St New Renovation
Dining

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
Sugar Shack - 300 square feet of pure sweetness.
Outdoor dining

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.

Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Hudson’
The price is HK$1,368
HK$2,330 total
includes taxes & fees
9 Jun - 10 Jun
Pet friendly 3-bedroom. About a mile from downtown. Fenced-in backyard.
Interior

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is HK$1,340
HK$3,273 total
includes taxes & fees
2 Jun - 3 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (4 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is HK$1,567
HK$2,650 total
includes taxes & fees
4 Jun - 5 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Pool

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson

Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Hudson
10.0 out of 10, Exceptional, (6 reviews)
"Our host was fantastic! She allowed us to check in early and check out late. The house was cozy and perfect for my girls weekend! "
United States
Kim W.
The price is HK$1,763
HK$4,054 total
includes taxes & fees
2 Jun - 3 Jun
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
Terrace/patio

BLUSH: Boutique TINY home*private spa*walk to town

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"The place exceeded expectations. Clean, cute space. Roomier than expected. Hot tub was on and at a good temperature. The Main Street with restaurants and bars is literally a 4 minute walk, yet the house feels secluded in a good way. Really enjoyed our stay."
United States
jack h.
The price is HK$1,959
HK$2,492 total
includes taxes & fees
31 May - 1 Jun
BLUSH: Boutique TINY home*private spa*walk to town
Private kitchen

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is HK$1,354
HK$3,289 total
includes taxes & fees
1 Jun - 2 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
Exterior detail

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]

Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Hudson
10.0 out of 10, Exceptional, (7 reviews)
"Nice house, decorations well done… communications with host were answered very quickly!"
United States
Brittaney O.
The price is HK$2,523
HK$4,710 total
includes taxes & fees
1 Jun - 2 Jun
Bespoke Design, Hot Tub, Fire Pit, Secluded Area & Projector [The Spring House]
Exterior detail

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (2 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is HK$1,567
HK$3,949 total
includes taxes & fees
31 May - 1 Jun
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is HK$2,108
HK$2,660 total
includes taxes & fees
31 May - 1 Jun
rural, serene + sophisticated space
Fridge, microwave, oven, stovetop

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
The price is HK$2,758
HK$5,467 total
includes taxes & fees
31 May - 1 Jun
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Pool

Charming Hudson Valley Escape | Heated Pool & Fire Pit

Charming Hudson Valley Escape | Heated Pool & Fire Pit
Claverack-Red Mills
The price is HK$2,857
HK$5,953 total
includes taxes & fees
4 Jun - 5 Jun
Charming Hudson Valley Escape | Heated Pool & Fire Pit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Columbia County Hotel Reviews

Howard Hotel

Howard Hotel

10/10 Excellent
"This hotel is a terrific value for the price! Our room was exceptional - clean, spacious, well-decorated, great ambience. The building is also ideally situated right in town, within easy walking distance of all the shops and restaurants. The only slight downside, if any, is the self-check-in - there's no front desk reception - but we didn't find it to be much of an inconvenience. A friendly manager/ staff person was around to answer our questions. Overall, we had no complaints and a very pleasant stay at the Howard."
Noel 1-night trip
Posted 3 hours ago
Howard Hotel