Holiday rentals with outdoor seating in Pioneer Valley

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

Top-rated Holiday Houses with Outdoor Seating in Pioneer Valley

Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Top Guest favourite

Cottage in Petersham

4.99 out of 5 average rating, 206 reviews

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

Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 426 reviews

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

Top Guest favourite

Guest suite in Village of Pelham

4.99 out of 5 average rating, 124 reviews

A Cosy Bijou Retreat Under The Hemlocks

Escape to a bijou, open-plan retreat under the hemlocks. This cosy, scent-sensitive-friendly gem is packed with amenities and bespoke touches throughout. Enjoy restful nights in a dreamy bed, a bespoke kitchenette, and a modern bathroom oasis. Features airy cathedral ceiling and clever space-saving design. Step outside to a courtyard with firepit, bistro dining, grill, outdoor prep kitchen, or the unique off-grid writer’s retreat. Fast Wi-Fi, guest-only parking, minutes to UMass and Amherst.

Top Guest favourite

Guesthouse in Cummington

5 out of 5 average rating, 112 reviews

Clark 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!

Guest favourite

Cabin in Cummington

4.98 out of 5 average rating, 224 reviews

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.

Top Guest favourite

Guest suite in Williamsburg

4.98 out of 5 average rating, 273 reviews

Happy Maples!

I am a custom builder and I decided to have some fun building out my own special guest space. Welcome to Happy Maples! The suite is a private 600 sq ft hand crafted studio with private entrance, bath w/shower, large deck w/Adirondack chairs and grill, views of the gardens and 100' from the historic Mill River right behind the house. There is a queen bed and an additional twin memory foam bed available. 12 mins to Northampton, 20 mins to Amherst, Bike trail in back yard. Come for a fun visit!

Guest favourite

Guest suite in Easthampton

4.92 out of 5 average rating, 272 reviews

The Floating Library: private hiker's hideaway

Spacious enough for a small family, cozy enough for a couple, a perfect alternative to a hotel, for exploring New England, or holing up to finish that book (reading or writing). TFL is a welcoming, above the garage in-law suite with a private entrance, full kitchen, full bath, laundry room, and lots of magical touches that will make your stay comfortable, unique and memorable. The location is right at the foot the hiking trails of Mt. Tom, a 20 min walk to idyllic downtown Easthampton.

Top Guest favourite

Tiny home in Northampton

4.99 out of 5 average rating, 220 reviews

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.

Top Guest favourite

Apartment in Northampton

4.98 out of 5 average rating, 382 reviews

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.

Top Guest favourite

Guest suite in Belchertown

4.98 out of 5 average rating, 143 reviews

Serene 1-br suite on 65 acre horse property

Enjoy nature while staying in a quiet 1 bedroom attached suite on a 65 acre horse property with it's own nature trails. It includes a private entrance with a dedicated workspace with free high-speed WiFi. Remote workers are welcome! We have up to 20 horses on the property. You will have front row viewing to several right out your windows! It's set back in the woods about a 1/3 of a mile, however it is a convenient location close to Amherst, Hampshire, UMass, Smith and Mt. Holyoke.

Top Guest favourite

Apartment in Northampton

4.98 out of 5 average rating, 725 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Top Guest favourite

Apartment in Northampton

4.99 out of 5 average rating, 173 reviews

Cozy Haven: Convenience & Charm

Welcome to our charming Florence, Massachusetts Airbnb! Only 10 minutes from downtown Northampton, our newly renovated property blends comfort, convenience, and natural beauty. Our location provides swift access to Northampton's vibrant heart. Within a 10-minute drive, you'll be amid bustling streets with eclectic shops, superb dining, and a lively arts scene. Explore boutiques, galleries, and cafes that define Northampton's creative and entertaining spirit.