House vacation rentals in Whitingham

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Popular amenities for Whitingham house rentals

House rentals with a pool

Guest favorite
The farmhouse features a classic two-story white exterior with green shutters and multiple windows. Snow covers the ground in front, while the entrance is highlighted by a center door flanked by sidelights. A gentle landscape with shrubs is visible on either side.
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars3 months ago
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!
Guest favorite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars3 weeks ago
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!
Guest favorite
A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars6 days ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Top guest favorite
An outdoor pool is surrounded by a spacious deck, featuring numerous lounge chairs. A children's playground is visible nearby, nestled among trees and greenery. The scene captures a serene atmosphere, ideal for relaxation and family enjoyment.
Home in Wilmington
4.96 out of 5 average rating, 27 reviews

Family/Dog Friendly Mountain Home w/ Amenities

ReutRating, 5 stars2 weeks ago
The house was just outstanding!! Beyond our expectations. We had so much fun at the house with such great facilities and wonderful location.
Guest favorite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars2 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Superhost
An outdoor pool area features a large swimming pool surrounded by spacious concrete decking. Several lounge chairs are arranged neatly along the perimeter. Adjacent to the pool, a children's play structure is visible, set against a backdrop of green trees.
Home in Wilmington
4.79 out of 5 average rating, 57 reviews

Chimney Hill Home w/ New Hot Tub & Amenity Center!

CourtneyRating, 5 stars1 month ago
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!
Top guest favorite
A spacious property is visible under a pastel sky at sunset, showcasing a well-maintained lawn with distinct stripes. The charming house, featuring a large covered porch, is framed by vibrant gardens and trees, with rolling hills visible in the background.
Home in Lanesborough
5 out of 5 average rating, 22 reviews

Mountain Blossom Retreat by Evergreen Home

AlysonRating, 5 stars2 weeks ago
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.
Top guest favorite
The spacious living room features a large, sectional grey couch and a white armchair, arranged around a wooden coffee table. A brick wood-burning fireplace is situated against a wooden wall, with a mounted TV above it. The room is illuminated by warm lighting.
Home in Dover
4.98 out of 5 average rating, 52 reviews

Spring Getaway @ Mt Snow! Hike, Bike, Sleeps 8.

JessicaRating, 5 stars3 months ago
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

Guest favorite
A covered front porch features two rocking chairs with striped cushions and a small side table. A door is visible with a number displayed, and a trash bin is positioned beside it. Welcome mats are placed on the wood plank flooring.
Home in Monroe
4.95 out of 5 average rating, 19 reviews

The Camp

KristyRating, 5 starstoday
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.
Top guest favorite
A spacious living room features a large sectional sofa with decorative pillows, paired with a wooden coffee table. Natural light floods in through large windows, highlighting the hardwood floor. The adjoining dining area, visible in the background, includes a wooden table surrounded by several chairs.
Home in Wilmington
4.96 out of 5 average rating, 49 reviews

Vermont Village Retreat Near Mount Snow

TRating, 5 stars2 months ago
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!
Top guest favorite
The exterior of the home is shown, featuring a charming porch illuminated by string lights. Adirondack chairs offer a cozy seating area amidst well-tended greenery and a gravel driveway. A backdrop of trees and a clear sky suggests a tranquil setting.
Home in Wilmington
5 out of 5 average rating, 30 reviews

Rustic home near skiing & lakes, walk to downtown

KassRating, 5 stars2 weeks ago
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!
Guest favorite
A green grassy area is framed by a large tree on the left, with a bird feeder standing amidst a variety of plants. In the background, expansive fields and rolling hills are visible under a partly cloudy sky, suggesting a serene rural environment.
Home in Stamford
5 out of 5 average rating, 34 reviews

Comfortable Entire Farmhouse close to North Adams

LisaRating, 5 stars4 days ago
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!
Top guest favorite
The exterior of a bright blue house is shown, featuring a wooden deck with railing and multiple large windows. Surrounding trees with autumn foliage add color to the scene. The lower section of the house reveals a stone path and storage area beneath the deck.
Home in Wilmington
5 out of 5 average rating, 15 reviews

Downtown Wilmington Home

Stuart MalcolmRating, 5 stars2 months ago
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.
Guest favorite
A modern glass house is situated on a gently sloping hill, surrounded by towering trees. The structure features large windows that reflect the natural surroundings, allowing light to enhance the space. Soft grass covers the hillside, leading to the home's entrance.
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars6 days ago
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.
Superhost
A historic red farmhouse and adjacent barn are set against a clear blue sky, surrounded by lush green grass. Stone pathways lead to the house, highlighting the inviting porch, while vibrant foliage borders the property.
Home in Whitingham
4.93 out of 5 average rating, 70 reviews

The Amos Brown House.

PeterRating, 5 stars3 months ago
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!
Top guest favorite
The exterior of the home features a well-maintained yard framed by trees and bushes, with a gray metal roof and white siding. A welcoming porch is visible, inviting relaxation in the lush green surroundings.
Home in Whitingham
5 out of 5 average rating, 39 reviews

Stonehedge Farm family getaway - swim, ski, hike

KarinRating, 5 stars5 months ago
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

Superhost
A spacious living area features high vaulted ceilings with wooden beams. A plush sectional sofa adorned with patterned cushions is situated in front of a modern stone fireplace. Large windows allow natural light to fill the room, enhancing the cozy atmosphere.
Home in Wilmington
4.73 out of 5 average rating, 11 reviews

The Birdhouse Retreat w/Hot Tub

BeatriceRating, 5 stars3 weeks ago
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.
Top guest favorite
A welcoming living area features a pair of patterned armchairs and a cozy sofa positioned on a neutral area rug. A coffee table stands in front of the seating. A wood stove is visible next to a TV console showcasing a scenic display, and natural light filters through the window drapes.
Home in Stamford
5 out of 5 average rating, 9 reviews

Peaceful Retreat near Unique Animal Encounter

JenRating, 5 stars2 weeks ago
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!
Superhost
A two-story house is depicted, featuring dark wood siding and large windows. A welcoming entrance includes a wooden overhang and steps leading to a stone path. The surrounding landscape consists of lush greenery, complementing the home's serene setting.
Home in Wilmington
4.6 out of 5 average rating, 5 reviews

Total Privacy on 5 acres with Hot Tub, A/C, stream

JulieRating, 5 stars2 weeks ago
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!
Guest favorite
A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.
Home in Ashfield
4.98 out of 5 average rating, 57 reviews

An 18th century farmhouse

NateRating, 5 stars6 days ago
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!
Guest favorite
A bright living area is furnished with a brown leather chesterfield sofa and a wooden coffee table. A vibrant rug adds warmth to the wood floor. Large windows offer views of the surrounding hills, while a cozy wood stove provides a focal point in the room.
Home in Brattleboro
5 out of 5 average rating, 7 reviews

4 BR home surrounded by hiking w Amazing views!

AamaniRating, 5 stars1 week ago
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!
Top guest favorite
The exterior of the cottage is partially obscured by tall, colorful wildflowers swaying in the breeze. Sunlight illuminates the scene, highlighting the serene setting surrounded by greenery and trees, with a clear blue sky in the background.
Home in East Dover
5 out of 5 average rating, 50 reviews

Magical Retreat Cottage - Waterfalls Everywhere

DavidRating, 5 starstoday
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.
Top guest favorite
A spacious deck overlooks a vibrant sunset, with an expansive view of rolling hills and trees under a partially cloudy sky. The area is enclosed by modern railing, and the deck's surface provides ample space for relaxation or gatherings.
Home in Leyden
5 out of 5 average rating, 15 reviews

Mountaintop Views, close to private schools, golf

JasonRating, 5 stars6 days ago
Beautiful property! Fantastic deck and views, and spacious and modern inside. Great place for a weekend with friends!
Guest favorite
The exterior of Chickadee Cottage is shown, featuring a blue shingle facade and large windows. A deck with railings provides an entry area, and surrounding greenery enhances the natural setting. A pathway leads to the entrance, inviting guests into the house.
Home in Woodford
5 out of 5 average rating, 29 reviews

Bright airy cottage w/ lake view

VickiRating, 5 stars2 weeks ago
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!

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