
Pet-friendly holiday rentals in Hampshire County
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Top-rated pet-friendly home rentals in Hampshire County
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The cozy clubhouse
Take a break and unwind at this peaceful cozy studio apartment with a private deck looking out over the garden and classic New England stone wall. Located on a quiet dead end street in the village of Haydenville. Not far from the local rail trail, hiking trails, and only a 13 minute drive to downtown Northampton. Very close to Look Park and Valley View Farm common wedding venues. A gateway to the Berkshires, with easy drive access to the Tanglewood music venue, Mount Greylock, and Mass MOCA.
4.97 out of 5 average rating, 189 reviews
Mill River Cottage (pet friendly!)
Welcome to our peaceful and unique urban farm cottage. We are located in historic Florence, Massachusetts (a part of Northampton). While our place is no longer a working farm, the cottage was created many years ago to support the main dwelling. It has been modernized to offer every comfort while maintaining its cozy aesthetic. Free parking & lighted access to the cottage. The cottage is a private space where you can come and go as you please. Relax and unwind or head out to explore the area!
4.99 out of 5 average rating, 443 reviews
Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.
4.95 out of 5 average rating, 320 reviews
Private Studio for a Sweet Getaway!
A cozy, comfortable, studio flat with ready access to local music venues and restaurants. Downtown Northampton is 15 mins by car or a 1/2 hr bike ride. We abut the bike path and there's a Valley Bike Share kiosk nearby. Ideal overnight spot for visiting Smith and other area colleges or for attending workshops at Snow farm. Easy day trips the Berkshires. Plenty of area hiking! Perfect personal retreat spot! I accept dogs on a case by case basis, small dogs preferred and I cannot accept cats.
4.98 out of 5 average rating, 172 reviews
Hadley Hay House | No Cleaning fees!
Rest easy in this picturesque, very spacious tranquil home ready for you for a relaxing stay. Minutes from umass, 10min to either Amherst or Noho. Not only will you have access to the hot tub and walk in the hay fields behind the house but we are directly across from the Connecticut River. Perfect spot for swimming or kayaking. Enjoy a beautiful view of the mountains/hay and corn fields from multiple rooms in the house. This space is above an all female wood working shop, happy to give tour!
4.96 out of 5 average rating, 168 reviews
Serene 1-br suite on 75 acre horse property
Escape to a peaceful 1-bedroom suite on a beautiful 75-acre horse property. Tucked into the woods 1/3 mile from the main road, enjoy privacy, scenic nature trails, and views of up to 20 horses grazing in the pastures outside your windows. Relax in the guest gazebo with front-row views of the horses, perfect for morning coffee or unwinding outdoors. Enjoy a private entrance, dedicated workspace, and high-speed WiFi. Conveniently near Amherst, UMass, Smith, and Mount Holyoke Colleges.
4.98 out of 5 average rating, 174 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.
4.98 out of 5 average rating, 308 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.
4.97 out of 5 average rating, 496 reviews
The Suprenant House
Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.
5.0 out of 5 average rating, 185 reviews
Garden Apartment in Northampton
Serene garden apartment in our two-family home, private entrance. A short 7-minute walk from vibrant downtown Northampton and its rich selection of eateries, shops and culture. Ideal for visiting local colleges. Seeking outdoor activity? You will be two short blocks from an access point to the Northampton Rail Trail Network, and the Pioneer Valley's natural beauty is easily accessible by car for walking and hiking. We offer off street parking for two cars in our driveway.
4.99 out of 5 average rating, 150 reviews
The Walnut Apartment
This beautiful and sunny 1 bedroom apartment is perfect for your stay in downtown Northampton, Massachusetts. It is walking distance to the Amtrak train station, all downtown restaurants and venues. Perfect for a stay to visit Smith College. You will find the beautiful claw foot tub perfect for relaxing after a day spent in the beautiful Pioneer Valley. This fully furnished apartment has a full kitchen, full bathroom, new furnishing, queen sized bed and its own entrance.
4.93 out of 5 average rating, 112 reviews
The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John
4.93 out of 5 average rating, 585 reviewsPopular amenities for Hampshire County pet-friendly home rentals
Pet-friendly house rentals

Historic Williams House
4.94 out of 5 average rating, 213 reviews
Stone n' Sky Lodge
4.91 out of 5 average rating, 254 reviews
Cozy lakehouse
5.0 out of 5 average rating, 119 reviews
Magical, Rural Getaway in the Berkshires
4.95 out of 5 average rating, 106 reviews
Tulsi Rose Healing Retreat
4.87 out of 5 average rating, 113 reviews
Beautiful, quiet and cozy home in Becket!
4.94 out of 5 average rating, 156 reviews
Entire 1-st Floor Apt & Specials
4.94 out of 5 average rating, 165 reviews
Farmhouse on working dairy farm
4.98 out of 5 average rating, 64 reviewsPet-friendly home rentals with a pool

Enjoy every season the Berkshires have to offer.
4.96 out of 5 average rating, 134 reviews
Sunset Ridge
4.95 out of 5 average rating, 62 reviews
Sweet cape near U Mass
4.87 out of 5 average rating, 38 reviews
Perfectly Polished Deerfield Home 5 min to I-91
4.81 out of 5 average rating, 267 reviews
Dog friendly, 2 fireplaces, Pool, Pickleball, 3 bd
4.94 out of 5 average rating, 18 reviews
NE Historical Mansion-pets and pet lovers welcome
4.81 out of 5 average rating, 321 reviewsPrivate, pet-friendly home rentals

Roost House (2 BR Apt. downtown)
4.95 out of 5 average rating, 375 reviews
Cozy Hilltown Cottage
4.99 out of 5 average rating, 222 reviews
Forest Hideaway—Light, Privacy, Washer/Dryer
5.0 out of 5 average rating, 119 reviews
Sunny Chalet Nestled in the Woods of Ashfield
5.0 out of 5 average rating, 154 reviews
Swiss Chalet Style Timberframe Home in Berkshires
4.93 out of 5 average rating, 311 reviews
Bright Private Studio | Walk to Smith & Downtown
4.93 out of 5 average rating, 133 reviews
Zachariah House Main St. Ashfield
4.88 out of 5 average rating, 297 reviews
Cedar Wet Room w Soaking Tub
4.95 out of 5 average rating, 279 reviewsDestinations to explore
- Rentals with pools Hampshire County
- Family-friendly rentals Hampshire County
- Guest house rentals Hampshire County
- Rentals with a hot tub Hampshire County
- Rentals with lake access Hampshire County
- House rentals Hampshire County
- Bed and breakfasts Hampshire County
- Rentals with breakfast Hampshire County
- Flat rentals Hampshire County
- Rentals with beach access Hampshire County
- Rentals with a kayak Hampshire County
- Private suite rentals Hampshire County
- Pet-friendly rentals Massachusetts
- Pet-friendly rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Monadnock State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- University of Connecticut
- Taconic State Park
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Dcu Center
- Ski Sundown
- Mount Monadnock
- Clark University
- Naumkeag
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- Hancock Shaker Village
- Mount Holyoke College
- Naismith Memorial Basketball Hall Of Fame
- Connecticut Convention Center





