
House holiday rentals in Whitingham
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Top-rated house rentals in Whitingham
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House rentals with a pool

Magical Farm Getaway - a must visit!
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

The 1770 House
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

The Brick House on Washington Street
Great stay and was exactly what we needed for our entire family for a weekend wedding!

Family/Dog Friendly Mountain Home w/ Amenities
The house was just outstanding!! Beyond our expectations. We had so much fun at the house with such great facilities and wonderful location.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

Chimney Hill Home w/ New Hot Tub & Amenity Center!
Stayed here as three couples with two dogs and had so much fun. We never left the home because it was so relaxing and enough to do right at the air bnb. Whether we were having a fire, going in the hot tub, playing pool, or making dinners together in the huge kitchen! We will definitely be back!

Mountain Blossom Retreat by Evergreen Home
We selected this amazing property as the location for our mini-wedding and we could not have been happier. The house is brilliant in every way. The floor plan, the furnishings, the decor, and the grounds are all thoughtful and stunningly beautiful. The property manager was always responsive and kind. This is truly a top property and you will not be disappointed. We cannot wait to visit again.

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.
We had such a great time staying here! The house was so cozy and clean and was perfect! Felt like being at home and not staying in an Airbnb. Super close to the mountain, especially if you park in carinthia! Loved the guest book that they have in the kitchen, a fun added touch! Robert was extremely responsive to any messages and super accommodating with us and our needs! Absolutely would recommend staying here!!
Weekly house rentals

The Camp
Great value for the price. Four guests plus my pup stayed at Marie’s place. All the comforts of home. Everything for meal prep was provided. Bathroom was stocked with plenty of towels and washcloths. Wifi worked well. Beautiful sound of the river right in the back yard was a bonus. Was a perfect base camp for us to look at possible land to buy in the future. Will definitely be back to continue our search.

Vermont Village Retreat Near Mount Snow
Matt's Airbnb was a wonderful place for us to get away for a long weekend! The house was lovely with all the comforts of home. We loved so much about this house, especially the layout. All one floor, which was great! The mudroom was great for bags and boots, the kitchen was well stocked , and the living room was amazing- very comfy large sectional sofa for relaxing, a nice cozy little sun room to hang out on and read a book. Having 3 bedrooms and 2 baths were the perfect size, and the washer and dryer were an added bonus. We loved the outdoor space for grilling and walking our pups. Very peaceful neighborhood and wonderful little town with great restaurants! Matt was so nice and helpful with any questions that we had, and even offered us a later check out which was nice! We loved this part of VT and hope to visit again soon! Thank you Matt for being such a great host! We can't wait to book our next stay!

Rustic home near skiing & lakes, walk to downtown
Very welcoming home, amenities were a great way to entertain ourselves during the night while kids were sleeping. The spacious living room, dining room and kitchen were an absolute dream! Would stay here again!

Comfortable Entire Farmhouse close to North Adams
We can’t say enough about the comfort and beauty of this home. Maura communicated with us regularly and provided coffee, tasty treats for breakfast, and snacks! The kitchen is fully stocked and was very helpful for our family to make our own meals. Sleeping on the porch was a joy! . I’m glad we got to briefly meet Maura; if we ever come back to the area, we hope to stay here again!

Downtown Wilmington Home
Alex was very easy to work with. He was very responsive and helpful. the house is in an outstanding location within walking distance to restaurants and shops. the house is very comfortable and well stocked with everything you need.

Vermont Mirror House
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

The Amos Brown House.
This is a really special antique house that has been very well cared for. we visited in the midst of pretty narly presidents dy snow storm and the howling winds and multiple feet of snow outside only made the old house feel even cozier and more special. in the winter, the house sits on the end of a dirt road, due to the southern portion of it being covered in snow so we were nervous that we would get completely snowed in, but the town plowed the road multiple times each day and we had no problems getting in and out! Our big highlights were cross country skiing on the trail that crosses the property, puzzling by the gas fireplace, and the huge mounds of dog toys for our pup! Also, big thank you to Michelle for being so accommodating about our late check out. Our time here makes me want to check out all of the landmark trusts locations!

Stonehedge Farm family getaway - swim, ski, hike
Every review for this property is spot on - a beautiful home in a fabulous location! We enjoyed everything the home had to offer - reading by the fireplace, playing air hockey, skating on Gates Pond, walking the snowmobile trails, sleeping late in comfortable beds, and just enjoying the surroundings. Marah and Liz were incredibly responsive, and graciously let us know that we could arrive prior to check in time. We would love to stay here again, and have already recommended the property to others!
Private house rentals

The Birdhouse Retreat w/Hot Tub
We had a great stay! The place was perfect, had plenty of space. Particularly loved the coffee bar which was well stocked. We took a day trip to Mass MOCA which was only about 30-40 minutes away.

Peaceful Retreat near Unique Animal Encounter
Daniel's place was the perfect home base for our Berkshires getaway. We visited Mass MoCA and loved coming back to this quiet, peaceful retreat. The backyard was especially serene, I enjoyed my morning coffee outside and relaxing by the fire at night. One of my favorite parts was cracking the window open and falling asleep to the soothing sound of the brook out back, pure magic. Daniel was a gracious host, friendly, responsive, and thoughtful. The local charm added so much to the experience, including camels and other farm animals across the street, Farmer Dave is a gem. We'd happily stay here again!

Total Privacy on 5 acres with Hot Tub, A/C, stream
We had a wonderful Memorial weekend stay at Emilio’s. The house was big and set up nicely. We were only traveling with 5 people but it could comfortably sleep 10. The yard was big and great for our dog to play in. The river in the back yard was a source of entertainment and rustic beauty for us and the kids. Emilio was responsive and helpful. Great place to set out on lots of local hikes. Hoping to return there for a ski trip someday!

An 18th century farmhouse
What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!

4 BR home surrounded by hiking w Amazing views!
Cal and Jackie’s place is GREAT! A little Vermont oasis. The view is exactly as the pictures show - the kitchen is wonderful for families fully equipped with a big dining table to go along with it. The place is cozy and exactly what we were looking for!

Magical Retreat Cottage - Waterfalls Everywhere
Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Mountaintop Views, close to private schools, golf
Beautiful property! Fantastic deck and views, and spacious and modern inside. Great place for a weekend with friends!

Bright airy cottage w/ lake view
We had a great time at the Chickadee over Memorial Day weekend! The weather wasn’t totally in our favor so sadly we couldn’t enjoy the nearby lake, but we filled our time with short trips into Bennington and Wilmington. The sunroom is a great spot to relax and the beds are super comfy! We were bummed that the outdoor shower had broken right before our stay, but Sarah did her best to try to get a handyman out and offered us a small discount when it couldn’t be fixed. We’ll just have to come back another time to enjoy all of the outdoor amenities!
Destinations to explore
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- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Norman Rockwell Museum
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Naumkeag
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Otis Ridge
- Canterbury Farm