A misty forest landscape with a hill in the background.

Craryville Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Craryville vacation rentals

Terrace/patio

1. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
$339 nightly
The price is $380
Sep 22 - Sep 23
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
Smart TV, books

2. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Pool

3. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
$340 nightly
The price is $381
Sep 22 - Sep 23
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
TV, fireplace, printers

4. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
$1,193 nightly
The price is $1,332
Sep 22 - Sep 23
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds

5. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (60 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Sep 27 - Sep 28
Total with taxes and fees
All comforts of home
Property grounds

6. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (37 reviews)
"Great location and super welcoming "
United States
Julie B.
$126 nightly
The price is $141
Sep 22 - Sep 23
Total with taxes and fees
All the comforts of home
Exterior

7. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (175 reviews)
"Great little place."
United States
Kim
$139 nightly
The price is $155
Sep 22 - Sep 23
Total with taxes and fees
Micosta Leisure Inn
Exterior detail

8. Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren

Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
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.
$420 nightly
The price is $475
Oct 14 - Oct 15
Total with taxes and fees
Designer Hudson Home: Hot Tub, Fire Pit, Projector & Walk to Warren
Coffee/tea maker, fridge, microwave, oven

9. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.6 out of 10, Exceptional, (4 reviews)
"Great location, great property, great host"
United States
Shelly B.
$148 nightly
The price is $165
Sep 28 - Sep 29
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
Coffee/tea maker, fridge, microwave, oven

10. Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren

Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren
Hudson
$812 nightly
The price is $918
Oct 20 - Oct 21
Total with taxes and fees
Designer Hudson Home: 4 Bedrooms, Loft, Parking & Walk to Warren
3 bedrooms, iron/ironing board, WiFi, bed sheets

11. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
$650 nightly
The price is $726
Sep 23 - Sep 24
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Beach nearby, sun loungers, beach towels

12. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (4 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
$271 nightly
The price is $303
Sep 23 - Sep 24
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Property grounds

13. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (44 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$394 nightly
The price is $440
Oct 12 - Oct 13
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Coffee/tea maker, fridge, microwave, oven

14. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
$294 nightly
The price is $329
Sep 24 - Sep 25
Total with taxes and fees
Home in Great Barrington
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (14 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
$305 nightly
The price is $342
Sep 22 - Sep 23
Total with taxes and fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Interior

16. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
$290 nightly
The price is $324
Oct 11 - Oct 12
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio

17. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
$327 nightly
The price is $366
Sep 22 - Sep 23
Total with taxes and fees
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Coffee/tea maker, fridge, microwave, oven

18. 2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend

2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Stottville
$675 nightly
The price is $756
Sep 22 - Sep 23
Total with taxes and fees
2 FUN homes w/ 2 Hot Tubs | 4BR, 2BA | PET Friend
Interior

19. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (26 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
$270 nightly
The price is $302
Sep 23 - Sep 24
Total with taxes and fees
Riverside Retreat in the Berkshires
Pool

20. 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, (10 reviews)
"Beautiful house and wonderful host. I very much hope we get to stay again in the future. "
United States
Jeffrey D.
$372 nightly
The price is $417
Oct 13 - Oct 14
Total with taxes and fees
Blue Heron House - 3BR Creekside Retreat with Hot Tub, Firepit & 10min to Hudson
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 Craryville Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Very nice stay. Nice town to stay in."
Wendy L 1-night trip
Posted 6 hours ago
Quality Inn Great Barrington

Find out more about Craryville

Everything you need to know about Craryville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Craryville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Craryville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Craryville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Craryville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Craryville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Craryville rentals

At Expedia, we put the best Craryville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Craryville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Craryville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Craryville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Craryville?

Yes, we have vacation rentals near the most popular sights in Craryville, or you can select a more secluded option if you're looking for relaxation. Craryville is known for its restaurants.

What's the top vacation rental in Craryville?

Catskill Cottage Walk to Downtown & River Views: You might want to consider this vacation rental near Craryville, which offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Craryville?

Expedia has 21 vacation rentals for your stay in Craryville.

What’s there to see and do in Craryville?

Explore the area and family-friendly sights such as Harney and Sons Tea Tasting Room, or get out into nature at a spot like Copake Lake. Catamount Aerial Adventure Park and Catamount Ski Area are a couple of places you'll find in the larger area.

What’s a vacation rental in Craryville like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Craryville. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.