
Vacation rentals with outdoor seating in Pioneer Valley
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Top-rated outdoor seating rentals in Pioneer Valley
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House rentals with outdoor seating

Charming home ready for fun and/or relaxation!
We came to Norfolk for a show at the Infinity Music Hall. This house was a perfect landing spot to cook dinner before and relax after the show. It was so peaceful watching the snow fall from inside and the kitchen was perfectly stocked with everything we needed to cook. The appliances were top notch, the house was well decorated and we will definitely rent here again!

Spacious 3 Bedroom Ranch With Office
We had a wonderful stay at Vasily’s home. The host is a responsive host and the home is uncluttered, which helped us easily navigate the new environment with young children. South Windsor has a lot to offer, with its long rural roads leading to well-made public parks and well-designed commercial areas. The Library is impressive, and the expansive children’s department is actually on its own floor. The tenant on the lower level of the home was friendly and helpful to us in a pinch, which we certainly appreciated. It was a lovely place, and we would certainly consider it again should life ever bring us back to South Windsor. Many thanks.

Central Haus (Group getaway on a quiet street)
Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

Lux on the River near Tanglewood w/220v EV charge
My friend and I had a lovely two-night stay at Julie's place. The house is the perfect retreat—peaceful, cozy, and beautifully located. We especially enjoyed the evenings by the wood-burning stove and long, leisurely breakfasts on the porch while listening to the river. The beds were incredibly comfortable, with high-quality pillows and bedding—we both slept so well! I would definitely love to come back someday with my husband to enjoy the peace and quiet, as well as everything else the Berkshires has to offer. Thank you, Julie and Arthur, for sharing your wonderful home with us!

State Forest Getaway
Elena's house turned out to be a great vacation spot for us. It was conveniently located, very well maintained and guest friendly. Though rustic on the outside, the interior was completely redone, offering all modern amenities you might want. Kitchen was better equipped than most Airbnb's we've stayed at and was fun for us to cook in Without getting into much detail I'll just say that should we be in the area again we'll definitely return to this Airbnb and always recommend it to others

Modern Spacious Home with Mountain Views
My family of four loved Christine’s place! She is so thoughtful, leaving yummy snacks plus necessities as well. She’s a great baker and provided us with some yummy treats! The beds were super comfy and cozy, bathrooms were clean and well-equipped and we loved being both close to downtown but also could go hiking out the back door. We feel so grateful to have had such a lovely and relaxing place to stay. Thank you, Christine! ❤️

Bernie's & Betty's
We stayed for a few days and the place worked out great! The kitchen is stocked with everything you’d need to include various paper products. Plenty of towels and linens for our family of 6. The entire home was very clean and well maintained. Great communication with Mike, and he even checked in on us to make sure we got settled without issue. We will definitely be staying here again when we travel back to North Adams!

Rabbit Run in the heart of Stockbridge Village
Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!
Apartment rentals with outdoor seating

Warm & Stylish Apartment w/laundry - walk to DT
Heather's place is amazing...very spacious and was great for my two week stay for work. It really great it is so close to the highway and also local restaurants and shopping. Will definitely stay again if I am in the area.

Modern Industrial Apartment with rooftop access
This Airbnb is so homey. We enjoyed our stay and will rent it again.

West Main
Exemplary accommodations! Everything about this place is well thought out and comfortable. (Every AirBnB host should do what Shirley did - label the light switches.) It's those intuitive touches that make this a great place to stay. We were close to family events in Norfolk, plus restaurants and amenities in Canaan. You really can't beat this experience. We were not able to make friends with the barn cat, but we tried!

Light filled three bedroom apartment DT Florence!
What a lovely place to stay! Great for families traveling with children. My kids loved the toys and the chickens in the backyard. :) The kitchen was very well stocked (plenty of cookware, dishes, tea, etc.). And Northampton is so cute with lots of fun things to do!

Quiet St in Town, gardens, terrace
We loved Jaki's apartment. It was very clean, neat, beautifully appointed, and convenient. Jaki welcomed us when we arrived and made herself available. She was friendly, warm, and very responsive. I'm returning to the area for business in the future and will book the same apartment again.

Apartment with a view
The quintessential Vermont Airbnb! Beautiful surroundings, lots of outdoor activities, and easy to get into town with great restaurants. The hosts are very helpful and provide everything needed for a relaxing stay.

Woodsy hideaway apartment
Very cute homey place in a beautiful setting, and a great value. Super convenient for visiting Amherst or UMass Amherst (just a couple blocks from UMass campus, and a very short drive to downtown Amherst). Great communication - Deborah messaged before we arrived to make sure we were good with directions and checked in while we were there to make sure we had everything we needed. She set us up with coffee, eggs, toast, juice, and homemade blueberry jam (!) - really nice. The apartment looks out into woods, and we woke up to a family of deer just chilling right outside.

River View Apt in Shelburne Falls Historic Village
Thanks Crystal It was a great spot for the weekend and very comfortable!
Condo rentals with outdoor seating

Pacer's Pasture
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

Spacious 3 bedroom apt in Lenox historic downtown
Beautiful apartment with lots of rooms-comfy sitting areas and lots of light. It was very nicely appointed and the checkin was simple. We will definitely be back as the location is ideal.

Flowers & Falls Spot House
Superhost ! Was so accommodating to get us in last minute since our other Airbnb didn’t work out. He was so responsive and helpful with the snow storm as well ! We were so glad to have found this gem and have such a gracious host. The location is perfect and walkable to all the restaurants and markets. Also 15 mins away from Berkshire East ! This was a great find and we are thankful for it !

Cozy Studio with patio, 1.2 mi from downtown
Beautiful stay at Goran's charming studio apartment. Thanks for the great communication!

Lovely 1bedrom apartment with screened in porch
Goran's home was very comfortable and we enjoyed many things. The architectural features were top notch with many luxurious details, such as the decorative tiles, the vaulted ceiling, and the large deck. We enjoyed the natural light, and the spacious rooms. The mattress was very comfortable, and we hope to return for another stay. I highly recommend Goran's home. Tracey deJong

Wyndham Bentley Brook
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Six Flags New England
- TPC River Highlands
- Taconic State Park
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Hartford Golf Club
- Douglas State Forest
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Brimfield State Forest
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Rockledge Golf Club