
Holiday rentals with outdoor seating in Pioneer Valley
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Pioneer Valley
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Cider House Cottage
Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Serene 1-br suite on 75 acre horse property
Find your peaceful retreat in our 1-bedroom suite, situated on a serene 75-acre horse property with scenic nature trails. Enjoy a private entrance, dedicated workspace, and complimentary high-speed WiFi, making it an ideal haven for remote workers. Take in the picturesque views of our horse pastures, with up to 20 horses, right from your windows. Our property is nestled in the woods, about 1/3 mile from the main road. Located near Amherst, Hampshire, UMass, Smith, and Mt. Holyoke colleges.

Cozy Hilltown Cottage
Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

In town, newly renovated studio with private deck
Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Tiny House Farm Retreat: Mountain Views, Fire pit
The Tiny House at Milestone Farm is a cozy farm retreat loaded with modern conveniences. Designed as a romantic escape for couples to relax and enjoy the tranquility of the farmlands while viewing the beautiful Holyoke range. Take in the amazing views and watch the many facets of commercial farming during the growing season. Create your own menu using our fully stocked kitchen. Meat and seasonal produce available for purchase in our farmstand. Minutes from the center of Northampton.

Sweet Retreat minutes from Northampton & Amherst
Our home is in Hadley, MA which is less than 5 minutes from Amherst and 10 minutes from Northampton. Amherst is home to the flagship campus of University of Massachusetts, Amherst College and Hampshire College. Northampton is home to Smith College and in nearby South Hadley is the campus of Mount Holyoke College. Hadley is known for it's farmlands and open spaces. Northampton is a vibrant arts community that overflows with great restaurants, shops, cafes, music venues and galleries.

Gorgeous Getaway
Brand new construction and state-of-the-art styling make this first-floor apartment a one-of-a-kind masterpiece. Every detail has been meticulously planned to ensure your visit is memorable! Just minutes from downtown Northampton, this stunning apartment features a spacious king-size bedroom with a private bath that includes a beautifully tiled walk-in shower, a second queen-size bedroom, a gorgeous kitchen with quartz countertops, and a beautiful living room with a flameless fireplace.

Light filled three bedroom apartment DT Florence!
Open floor plan duplex with beautiful back yard that has a patio, dog run, chickens, grill, fire pit, and fruit trees! One block from the corner store and the Pie Bar. If you enjoy cycling the bike path abuts the back of the property! Quiet neighborhood, pet and kid friendly one block from downtown Florence. Look Park is a mile down the bike path. Plenty to do if the weather is not cooperating. Fully appointed kitchen to make cookies, home made ice cream, plenty of games and records.

Large Studio – Walk to Town
IMPORTANT: Please read the full description about the eco-friendly policy and click the "CONTACT HOST" button, rather than making a reservation. I will respond very quickly to your request. Thank you for your consideration! A unique studio, loft-like, surrounded by beautiful gardens, a short walk to downtown and Smith College; perfect for visiting the five colleges, attending weddings, graduations, workshops, writing and research; close to hiking and bicycle trails.

A Country Retreat-Enhanced Studio Apartment
Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.
Popular amenities for outdoor seating rentals in Pioneer Valley
House rentals with outdoor seating

Victorian house near Smith college and downtown

Farm Fresh Feeding Hills

Charming Brookside Artisan Home

Lovely 2BR Home Close to Downtown

The Farmhouse - Hot tub eclectic farmhouse 3 br

Stone n' Sky Lodge

Sunrise on the Water's Edge - Riverside Bungalow

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Apartment rentals with outdoor seating

Warm & Stylish Apartment w/laundry - walk to DT

Sunny, light filled loft in 1873 Colonial

Suite 23 - Spacious Sunny 2-BR with Mountain view

Sunny Peaceful Home

Sunny carriage house apartment

Steps to MoCA Near SKI: 2bd + SAUNA!

House Above the Hollow

Western Mass Retreat!
Other holiday rentals with outdoor seating

Luxurious and Sunny Bedroom Suite!

Historic 1850 Farmhouse

Bright Noho studio suite perfect walk to downtown

Mountain View Cabin House

Pristine Oasis with Private Bath

Private Tiny House - Farm like setting

The Writer's Retreat: A Sweetwater Stay

Serene Modern Country Cottage near Amherst Center
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a hot tub Pioneer Valley
- Rentals with an EV charger Pioneer Valley
- Rentals with a fireplace Pioneer Valley
- Bed and breakfasts Pioneer Valley
- Cabin rentals Pioneer Valley
- Waterfront rentals Pioneer Valley
- Family-friendly rentals Pioneer Valley
- Rentals with lake access Pioneer Valley
- Rentals with pools Pioneer Valley
- Cottage rentals Pioneer Valley
- Rentals with breakfast Pioneer Valley
- Guest house rentals Pioneer Valley
- Pet-friendly rentals Pioneer Valley
- Rentals with a firepit Pioneer Valley
- Flat rentals Pioneer Valley
- Smoking-friendly rentals Pioneer Valley
- Rentals with beach access Pioneer Valley
- House rentals Pioneer Valley
- Rentals with a washing machine and dryer Pioneer Valley
- Private suite rentals Pioneer Valley
- Apartment rentals Pioneer Valley
- Rentals with a patio Pioneer Valley
- Rentals with a kayak Pioneer Valley
- Rentals with outdoor seating Massachusetts
- Rentals with outdoor seating United States
- Six Flags New England
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- TPC River Highlands
- Brownstone Adventure Sports Park
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Bushnell Park
- Brimfield State Forest
- Taconic State Park
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Bigelow Hollow State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bright Nights at Forest Park
- Talcott Mountain State Park
- Mount Sugarloaf State Reservation
- Butternut Ski Area and Tubing Center
- Dinosaur State Park
- Hartford Golf Club
- Beartown State Forest




