
House holiday rentals in Ashfield
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House rentals with a pool

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!

Adams Farm-"The Little Farmhouse"
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

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
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.

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.

Berkshire County modern home + pool
We had a wonderful stay at this adorable home in the Berkshires! The house was very comfortable and cozy, and the backyard with the deck and pool provided a wonderful space to hang out day and night. The house was situated 20-30 minutes from so many places - downtown Lenox, Miraval Spa and Ballderdash Winery. We can’t wait to come back!!

Morning Side
Morning Side is filled with character and charm. The house itself, the furnishings, and even the book collection take you back to 18th century New England. The kitchen and dining area are particularly cozy and inviting. The windows and views are magical, particularly with a good snowfall. The host was very helpful, particularly proactive about preparing the sidewalk and driveway for snowfall, even on Thanksgiving Day!
Weekly house rentals

Luxury log style home with views to Mt. Monadnock!
We had a wonderful stay at Debra's log cabin. Beautiful location, glorious and cozy home, and fun amenities. We played foos-ball and spent many lovely, peaceful hours in the cabin. Be careful in the winter/early spring as the walkways and driveway can get icy, but it's worth it to make it up them both.

Charming Brookside Artisan Home
This place was awesome. Would have enjoyed the outdoors and fire pit more if it didn’t rain. I would definitely recommend

Bridge of flowers cottage
Our family converged on Shelburne Falls from several faraway places for a nearby college graduation. We rented 5 nights in order to make it a family reunion. This lovely home turned out to be the perfect setting, as it has a large amount of common living space, in several adjacent rooms, so that we could be all together or in smaller groups. We enjoyed meals in the large kitchen, sitting by the fire, short walks to good restaurants and handy grocery stores. We sat on the porch enjoying the garden. The area is quiet and safe. The trains coming through at the bottom of the garden were entertaining, but didn't wake people up because the trains go very slowly through a sunken section and don't honk nearby. The town is delightful, and plenty of hiking and things to do (Clark Art Museum!) nearby. As longtime AirBnBers, what we appreciated most is that this is really a family home, with an attentive host and a helpful neighbor/manager. In other words, AirBnb at its best!

1810 Brook-Side Mill/EV 2 Charge
Comfortable, cozy, clean and peaceful house for our family of three. We each had a floor with a full bathroom, and great amenities throughout. We particularly loved being between great skiing at Berkshire East and the beautiful town of Shelburne Falls.

True Shangri-la, Country Retreat
My 11-day stay at Mary's was truly tranquil and restorative. The grounds are exquisitely maintained, full of color and delight. it was lovely to wake each morning see new blooms opening up into the day. The weather couldn't have been more perfect, allowing for outdoor meals & long afternoons reading on the back porch-the only sounds wind in trees, water in nearby streams, birdsong & in the evenings, the trill of peepers by the pond. all with the stunning view of the mountains in the distance. The house itself is beautifully appointed, furniture, beds, bedding and decor, all high quality. The kitchen is totally stocked with first-rate appliances, a joy to cook in. and I can say without any doubt, this is the only airbnb i've stayed in where the artwork and the books were EXCELLENT. Mary is the best kind of host- helpful, thoughtful, and incredibly responsive. Her attention to detail and kind consideration were likewise everywhere evident. I can't wait to return! thank you Mary!

The Walnut Apartment
Very cute apartment and more than what we needed for a one night stay on a wedding weekend! The downstairs has a charming sitting room and spacious kitchen with fridge, stove, and laundry. The stairs were a bit steep so be cautious! Upstairs a comfy soft bed with window AC and a large bathroom with clawfoot tub/shower. Jennifer was very nice about our last minute request to check in early to change for a 4 PM wedding. We would stay here again if we come back to the area! Thanks so much!

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.

Carriage House Studio
If you love the rural character of western Massachusetts with peaceful and lovely landscapes, this place is full of comfort and is very inviting! We had a wonderful time visiting!
Private house rentals

Nerd Preservation Sanctuary
My husband and I loved our stay at this house. It checked all our boxes. It was clean, spacious, had a comfortable bed, plenty of hot water and a barbecue grill. It also came with lots of personality. We ate breakfast at the local country store/cafe called Sherwood Forest most days. It was a great place to relax and enjoy the peaceful surroundings.

Moonstone Lake House – romantic, serene, fun!
Had a wonderful stay at Mighty’s house on the lake. It was such a peaceful and beautiful area. The house was clean and tidy with a spacious bathroom and comfortable bed. It was reassuring to have our hosts right next door but there was a good amount of privacy. We enjoyed the fire pit in the evenings, taking the canoe out on the beautiful lake and having some space and time to wind down. I highly recommend this home for anyone looking to step away from life for a little while.

Cambridge Hill Farmhouse - Sauna - Swimming Pond
This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.

Cute and Cozy Lake Cottage
While the weather was not optimal (sometimes western MA spring is slow to come), we loved the cottage. It is perfect for walking, hiking, reading and other quiet activities. But, you have access easily to Northampton or other local towns for a meal or night out. Debra was easy to reach but not at all intrusive. Check in was smooth. All in all, a lovely experience.

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!

Light-filled Lake House in Goshen
We had a wonderful stay at Carol and Robin’s home on the lake. Anyone looking for a serene and peaceful setting would be thrilled with this rental. Our hosts communication both prior to and during our stay was top notch. We certainly hope to return someday.

Colorful Urban Cabin Steps from Mass MoCA
Eli's home is in a great location; easily walkable to MassMoca and downtown. It's small but cute and has everything one needs to cook, rest, etc. There are a couple of things to be mindful of... - The upstairs bedrooms get quite hot in the warm weather, and the ACs are very loud, as is the fan. I highly recommend bringing earplugs; we only had one pair, and my husband didn't sleep well during the hot night (we both slept well the other nights!). This is not the first time we've experienced this at an Airbnb, and it would be super nice if hosts provided quiet ACs for their rentals. Eli is responsible, so I'm sure he'll figure out an alternative. The bed was very comfortable! - There are a lot of steep stairs (inside and out), which normally isn't an issue, but we were traveling with our heavy e-bikes and had to carry them up and down the stairs, and that kept us from going for several spontaneous bike rides. Overall, we enjoyed our stay at Eli's and would recommend his home.
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Brimfield State Forest
- Mount Snow Ski Resort
- Norman Rockwell Museum
- The Shattuck Golf Club
- Beartown State Forest
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards