Photo by Debbie Hall

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Featured Cottages in Buckland

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

9.0 out of 10, Wonderful, (42)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

3.0 star property
6.0 out of 10, (1)
"I tried to reach out to the contact given regarding some checkout procedures and got zero response. "
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort

Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

3.0 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!

Charlemont Retreat on Chickley River w/ EV Charger

3.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Cozy Treetop Hideaway Near Harriman Reservoir!

3.0 star property
Cozy Treetop Hideaway Near Harriman Reservoir!

Picturesque Cottage with Sunroom on Ashmere Lake!

9.4 out of 10, Exceptional, (21)
"Everything was just like it was listed. We had trouble with the t.v. but other than that it was great. "
Picturesque Cottage with Sunroom on Ashmere Lake!

'john's Farmhouse in Mount Snow' on 120 Acres!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Great for a family get away. Hosts were top notch. I stay in rentals all the time for work and this was great. I will bring my grand kids next time. "
'john's Farmhouse in Mount Snow' on 120 Acres!

Near Hiking & Skiing: Home in Wilmington!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Near Hiking & Skiing: Home in Wilmington!

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

3.0 star property
Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Black Bear Mountain Cottage

Black Bear Mountain Cottage

Hadley Vacation Rental 24 Mi to Springfield!

3.0 star property
Hadley Vacation Rental 24 Mi to Springfield!

Cozy Southern Vermont Home w/ On-site Trails

3.0 star property
Cozy Southern Vermont Home w/ On-site Trails

Rare new Home on Lake Whitingham. Semi-priv beach

Rare new Home on Lake Whitingham. Semi-priv beach

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!

Sleek Cabin w/ Deck, 8 Miles to Mount Snow & Hikes

3.0 star property
Sleek Cabin w/ Deck, 8 Miles to Mount Snow & Hikes

Private Wooded Cabin, 8 Mi to Sundance Ski & Town!

3.0 star property
Private Wooded Cabin, 8 Mi to Sundance Ski & Town!

Stylish cottage close to great hiking trails and great art museums

Stylish cottage close to great hiking trails and great art museums
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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Other property types in Buckland

6 Bedrooms, 2 Offices, Internet, River, New England village charm

9.6 out of 10, Exceptional, (58)
"Five of travelled to Massachusetts for a brewery tour and we decided to get a house instead of the usual hotel. We are glad we did! This house was as advertised with lots of charm and character. The age of the house was apparent but in a good way. It felt historical!"
6 Bedrooms, 2 Offices, Internet, River, New England village charm

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (68)
"This is our 3rd time staying here, we love this historic home, it is in very good condition. The home is very clean, well stocked, the layout is very good and the communication with the host is also very good. We love the brook going by. It is close to Smith College where our daughter goes to school. We also enjoy the many other places and things to do in this area. Even after our daughter graduates I can see us coming back to this home and part of Massachusetts. "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is AU$399
includes taxes & fees
24 Nov - 25 Nov
Cozy apartment located in quiet Williamsburg
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What is there to do in Buckland near my cottage?
No matter your interests, Buckland has plenty to keep you on the move. High Ledges Wildlife Sanctuary, Shelburne Falls Bowling Alley and Bridge of Flowers are on most visitors’ sightseeing itineraries. Don’t leave without exploring White Barn Studio, Bald Mountain Pottery and Bardwells Ferry Bridge either. With Expedia’s Buckland hotel deals, you can see even more popular attractions like these with the cash you save.