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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Whitingham Cottages

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

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

8.8 out of 10, Excellent, (44)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Exterior

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (132)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Exterior

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Lake life at Woodford Cottage
Smart TV, fireplace

Lake life at Woodford Cottage

9.4 out of 10, Exceptional, (13)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK
TV, fireplace, DVD player, books

Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and neat. Very quaint and in the woods. We had a great time. Looking forward to doing it again in the near future. "
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK
Cottage in Private Village On VT-100 (5-min to Mount Snow)
Fridge, microwave, oven, stovetop

Cottage in Private Village On VT-100 (5-min to Mount Snow)

10.0 out of 10, Exceptional, (1)
"I loved our stay here! The place is incredibly cozy. It’s in a fantastic location with great dining options just a few miles away. Plus, there are several nearby hiking trails with stunning views. Perfect for anyone looking to enjoy great food and outdoor adventures. Highly recommend!"
Cottage in Private Village On VT-100 (5-min to Mount Snow)
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (71)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
Bennington Gem w/ Smart TV Near Historic District!
House (1 Bedroom) | Private kitchen

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
Bennington Gem w/ Smart TV Near Historic District!
Hike & Swim On-site: Cozy Falls Brook Cabin
House (2 Bedrooms) | Interior

Hike & Swim On-site: Cozy Falls Brook Cabin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Hike & Swim On-site: Cozy Falls Brook Cabin
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
House (1 Bedroom) | Interior

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!
'john's Farmhouse in Mount Snow' on 120 Acres!
5 bedrooms, laptop workspace, free cribs/infant beds, bed sheets

'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!
Charlemont Retreat on Chickley River w/ EV Charger
Terrace/patio

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

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
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
House (3 Bedrooms) | Private kitchen

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
TV, video-game console, table tennis, books

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Near Skiing & Hiking: Quiet Home in West Wardsboro
Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior

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!
Jacksonville Cabin w/ Wraparound Deck & Views
House (3 Bedrooms) | Interior

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Luxury Vacation Rental in the Berkshires!
TV, fireplace, books

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Wilmington Retreat Near Trails, Skiing & Festivals
Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (1)
"Would definitely recommend! House had an everything we would need. So comfy and cozy! "
Wilmington Retreat Near Trails, Skiing & Festivals
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 Whitingham

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Vermont Lake Front Log Cabin Close to Mt. Snow
Exterior

Vermont Lake Front Log Cabin Close to Mt. Snow

10.0 out of 10, Exceptional, (64)
"I can’t say enough about our host, Bob, and this property. If you’re looking for a peaceful slice of heaven, this immaculate log cabin is the place. This is the cleanest rental we’ve ever stayed in and the attention to detail was incredible. The kitchen was super stocked and the furniture was comfortable, we immediately felt at home. The Firepit by the water was so relaxing and the fireplace inside was great to end the day. Thanks to Bob for the wood. Bob was extremely responsive and friendly,...
Vermont Lake Front Log Cabin Close to Mt. Snow
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (2)
"This place is somehow better than it looks online. It is truly spectacular. And incredibly easy ski in ski out. Ski in is right to the door and ski out is about 10 foot walk to the magic carpet in the backyard. Tina of room. First class appliances. Tons of parking. We had a big group. Also two great places to hang out upstairs in the great room then the kids needed up hanging out a lot on the main floor. Checking in was a piece of cake and Todd was very responsive if we needed anything. Can’t...
Brand new listing! True Ski In & Ski Out with Private Hot Tub & 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.

Frequently asked questions

Why book your cottage in Whitingham with Expedia?
Expedia has some excellent cottages in Whitingham, so start packing your bags for an unforgettable vacay on nature’s doorstep. If you have a budget in mind, select how much you’re willing to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with free WiFi or a kitchen. We’ll help you find the perfect fit whatever your style of travel or plans.
How can I find cheap cottages in Whitingham?
With Expedia’s useful filter tool, sourcing cheap cottages in Whitingham is easy. To find properties that are friendly on the wallet, tailor your search results by amenities, star rating and budget.