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Compare 391 Vacation Homes in Whitingham with updated reviews, rates, and availability.

"Absolutely loved my stay at this tiny getaway house! The space was cozy, well-designed, and had everything I needed for a relaxing escape. The peaceful surroundings and thoughtful touches made it truly special. Perfect for unplugging and recharging. Can’t wait to come back for another retreat!" "

Dover Vacation Rental | 2BR | 2BA | 1,350 Sq Ft | Stairs Required

"Location was perfect with the Moover transfer right on the door and even walking distance to the ski mountain(8’ walk). House was clean and had everything we needed. The only thing that could be better was the communication with the apt management/ owner. We couldn’t find the pool or hot tub and got no answer after asking. We had other questions that never got answered too. But overall for it was a great New year’s holiday!"

Stratton Vacation Rental | 3BR | 1.5BA | 1,100 Sq Ft | Stairs Required

"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...

"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...

The house was originally built in 1864 and completely updated in 2009

"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!"

Take in stunning views from our large windows while cozied by the fire

"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"

"The property has a great location to so many activities, shops and places to eat. The house was a few steps from the pool which my kids loved"

"Everything about this house was great! We will definitely be back!"

"Great house for the family. Easy to jump on shuttle and hit the slopes. Easy to just drop your bags and enjoy the view of the mountain. Comfy couches. Big dining table to gather around. Kitchen has everything you need. Well stocked with linens and towels. Owner was communicative and helpful."

"House looks exactly as it does in the photos. No real yard, but the house itself is very comfortable. Plenty of space, comfortable beds and accommodating common areas. We struggled with the Internet through the duration of our stay, due to storms in the area. The property managers were in constant communication with us, but couldn't get the Internet service provider to resolve the issue. House is less than 10 minutes from Stratton Mountain, which is great. Unfortunately, it rained for the...

Wardsboro Vacation Rental | 5BR | 2.5BA | 2,015 Sq Ft | Steps Required for Entry

"Perfect vacation rental! Very clean, comfortable beds and perfect for 2 families. We went during ski season so the mudroom was tight but adequate. We would definitely stay there again!"

"This property is newly renovated, exceptionally clean, well located next to the river, and uniquely decorated with owner created and produced items from dish sets to pillows and various artworks throughout the home. The hosts, Noelle and Eric, were extremely helpful with explaining the house and surroundings to us, and were always available for any questions or needs that we might have. A really exceptional house with gracious hosts nearby. Highly recommended and we hope to visit again."

Green River Cottage. Walk up ramp to enter patio area, lockbox on inside door.

"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...

Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...

"Great house in a great neighborhood for two families and our dog that wasn’t too far from Mt Snow. The clubhouse is a plus with a pool!"

Lush woodland setting is private, yet five minutes to Spring Street.

"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"

"We had the most enjoyable and comfortable stay at this lovely home away from home! Jen was more than welcoming and always very responsive. The house was very clean and located conveniently across the street from the mountains. Looking forward to staying here again next season! :)"

"This rental property was very clean and spacious. There is air conditioning upstairs and ceiling fans (which is hard to come by in this area). Great location. Highly recommend."