Pet-friendly holiday rentals in Springfield

4.93 out of 5 average rating, 536 reviews

A charming property is illuminated with colorful lights during the evening. The spacious deck is adorned with festive decorations, and a Christmas tree can be seen through large windows. The surrounding area is dark, emphasizing the warm glow of the lights.

Bungalow in Easthampton

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? Update! We just installed an 8 person hot tub! Plus our 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

4.95 out of 5 average rating, 123 reviews

The spacious studio apartment features a well-equipped kitchen with a countertop and bar seating. Natural light filters through the windows, highlighting wooden cabinetry and modern appliances. The open layout includes a cozy seating area, creating a functional living space beneath sloped ceilings.

Flat in Williamsburg

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.

Guest house in Northampton

The entrance features a white door with a windowpane design, framed by light blue siding. A decorative lantern hangs beside the door. A small potted plant rests on a blue chair, while a welcome mat adorned with black dogs is placed at the threshold.

4.99 out of 5 average rating, 381 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!

4.91 out of 5 average rating, 163 reviews

A welcoming exterior features a curved brick pathway leading to a front porch surrounded by neatly trimmed evergreen shrubs. Potted plants add color to the entrance, complemented by decorative hanging baskets. The home presents a classic facade with white columns framing the entrance.

Flat in Suffield

2 BR LR 1BA Private In-Law Suite with Home Theater

Suffield is a quaint New England town with a historic town center. Attractions: Six Flags, MGM Casino, Suffield Academy, Suffield Country Club, Basketball Hall of Fame, etc. 10 minutes from Bradley Airport. This ultra modern in law apartment is newly built (1350 sqft) in our walkout basement. Bright, contemporary, laminate flooring, game room & laundry. Luxury beds. Private entrance. Professionally sanitized for your protection. Complimentary Breakfast at Barista Cafe in Suffield Town Center.

Guest suite in Belchertown

A serene scene depicts several horses grazing in a fenced area, surrounded by vibrant autumn foliage. A charming white house is visible in the background, framed by trees under a clear blue sky. Natural light enhances the tranquil setting.

4.98 out of 5 average rating, 153 reviews

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.

Guest house in Cummington

A cozy sleeping area is highlighted by a spacious bed dressed in neutral linens. An inviting cushion rests on the bed, while warm light emanates from two bedside lamps. A wooden bench sits at the foot of the bed, and decorative greenery adorns the walls.

5 out of 5 average rating, 140 reviews

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!

4.98 out of 5 average rating, 245 reviews

A panoramic view of the expansive farmland stretches towards a distant mountain range under a colorful twilight sky. Two wooden chairs are positioned on the grassy area, providing a serene spot to enjoy the landscape.

Tiny home in Northampton

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.

4.97 out of 5 average rating, 407 reviews

A bright living area features wooden flooring and a blend of seating options, including a yellow sofa and patterned armchairs. A glass coffee table sits atop a decorative rug, complemented by artwork on the walls and natural light streaming through the window.

Flat in Northampton

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.

4.96 out of 5 average rating, 637 reviews

A vibrant red and orange tree stands beside a deep red building, showcasing the beauty of autumn foliage. The tree's colorful leaves contrast with the clear blue sky, while a parked car is visible in the foreground, adding to the peaceful residential atmosphere.

Barn in Northampton

Brookside Carriage House. Private, Great Location.

1890's Carriage House. Bright 850 sq. ft., 2nd flr. studio. Original wood flrs, 12' ceiling, skylights, modern amenities w/ rustic charm. Onsite parking. Two sleeping nooks: One QUEEN, One FULL bed & a leather couch; open floor plan. Shower, laundry, full kitchen, dining table, lounging area, Juliet balconey. Eclectic, spacious, private, quiet, all in a fantastic location. This is a large studio. Staircase to 2nd floor. No TV. Dog friendly; contact me first. Non-Smoking/vaping.

4.89 out of 5 average rating, 1,001 reviews

A welcoming entrance features a maroon front door with glass panes, flanked by a wooden railing. A slight wooden ramp leads up to the door, surrounded by a manicured area of small plants and gravel, creating an inviting first impression.

Home in Feeding Hills

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

4.95 out of 5 average rating, 105 reviews

The living room features a spacious sectional couch adorned with decorative pillows, complemented by a coffee table at its center. A cozy armchair with a contrasting cushion sits nearby. Natural light streams through two large windows, enhancing the warmth of the space.

Flat in Chicopee

Cozy Brick House in Chicopee

Relax with the whole family at this peaceful place to stay. The unit is part of a two family duplex house. You and your family will have the entire unit to yourselves. There are two bedrooms with queen size beds, a living room, kitchen, bathroom, and laundry room. The living room has a TV, fireplace, and Netflix. There is also a fenced in back yard with a patio and outdoor dining area as well as a firepit. The house is also pet-friendly.

4.94 out of 5 average rating, 101 reviews

The exterior of the house is shown, featuring light grey siding and a welcoming front porch with a wooden railing. A well-maintained lawn surrounds the property, with trees providing shade. A fenced-in area is visible to the side, enhancing the outdoor space.

Home in Springfield

Clean/Spacious 1 bedroom house. Kitchen, LR, DR.

You have the entire space to yourself. Newly painted. Newly refinished hardwood floors throughout. Dining room, Living Room and Kitchen and Front porch, back porch and fenced-in Backyard all for your use. ~Pet fee is $100 for up to 1 pet, $40 for additional pet[per night, they are added guests]~{please add them in your guest count, as I prepare for their stay, as well!} ~ MAXIMUM PETS ALLOWED IS 2 ~

Popular amenities for Springfield pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.87 out of 5 average rating, 101 reviews

Home in West Hartford

Charming home in West Hartford

4.87 out of 5 average rating, 105 reviews

A bright and inviting open-concept living area features two vibrant blue armchairs adorned with floral patterns. A wooden dining table is visible in the background, with a fully equipped kitchen displaying colorful cabinetry and modern appliances. Soft light enhances a welcoming atmosphere.

Home in Ashford

Lake - King - Gym - Kayak - Fire Pit - Pets Allowed - WD

4.89 out of 5 average rating, 166 reviews

A globe rests on a polished surface, accompanied by a wooden 'Hello!' sign. Sheer curtains filter soft light, creating a bright and welcoming scene. The composition offers a blend of decorative elements that enhance the living space.

Home in South Windsor

Spacious 3 Bedroom Ranch With Office

4.87 out of 5 average rating, 247 reviews

The image showcases a spacious green yard surrounding a charming gazebo. In the foreground, assorted seating arrangements invite relaxation. The background features trees in full bloom, enhancing the natural setting and providing a peaceful atmosphere.

Home in Brimfield

Little House Inn - Brimmy - Private Home

4.9 out of 5 average rating, 229 reviews

A view from above displays a cozy sitting area beneath exposed wooden beams. A rich, patterned rug covers the floor, while a plush armchair and a small table are positioned nearby. Natural light filters in through the adjacent windows, illuminating bookshelves filled with items.

Home in New Salem

Stone n' Sky Lodge

4.9 out of 5 average rating, 108 reviews

A charming red homestead is surrounded by a light coating of snow, with a wooden staircase leading to the entrance. Leafless trees are visible in the foreground, and a convenience store can be seen in the background, enhancing the house's accessibility.

Home in Torrington

Charming Home in Litchfield County on a MAIN ROAD!

4.83 out of 5 average rating, 112 reviews

A rustic cabin exterior is presented, featuring a stone chimney and wooden siding. Lush green grass surrounds the property, with a gravel driveway leading to the entrance. Trees provide shade, enhancing the tranquil outdoor setting.

Home in Ashford

Amazing lake home w/ amenities.

4.92 out of 5 average rating, 256 reviews

Home in Adams

1890 House

Pet-friendly home rentals with a pool

4.92 out of 5 average rating, 293 reviews

A game room is equipped with a pool table, illuminated by LED lights along the walls. A large screen displays options for entertainment. An arcade machine and various decorations enhance the playful atmosphere, while the wooden floor adds warmth to the space.

Home in Montville

Casino Wine Down House

4.89 out of 5 average rating, 134 reviews

A cape-style farmhouse is nestled beneath the expansive green canopy of a large tree. The house features multiple windows and a spacious deck, while the surrounding lawn is dotted with sunlight and shrubbery, creating a serene outdoor environment.

Home in Colrain

The 1770 House

4.84 out of 5 average rating, 120 reviews

The image captures a serene view of a clear pool reflecting the colorful sunset, framed by a meticulously paved patio. Two cabana beds are positioned next to the pool, with surrounding greenery and a decorative fence enhancing the outdoor space.

Flat in Burlington

Charming apartment with breathtaking view!

4.95 out of 5 average rating, 169 reviews

A majestic moose stands partially submerged in the calm waters of a pond, showcasing its prominent antlers. Lush greenery surrounds the area, creating a serene and natural atmosphere.

Cabin in Hubbardston

Triggers Cabin

4.8 out of 5 average rating, 258 reviews

A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.

Flat in Holyoke

NE Historical Mansion-pets and pet lovers welcome

4.96 out of 5 average rating, 119 reviews

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Flat in Otis

Enjoy every season the Berkshires have to offer.

4.93 out of 5 average rating, 196 reviews

A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.89 out of 5 average rating, 447 reviews

An open living space showcases a wooden table with candles, surrounded by wooden chairs. A white sofa with decorative cushions is positioned next to a reddish armchair. A coffee table sits central, with a small plant atop a patterned rug. Light illuminates the cozy atmosphere.

Flat in Glastonbury

Quiet 2 bed room apt w/ private entrance.

Private, pet-friendly home rentals

4.99 out of 5 average rating, 899 reviews

The exterior view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

Water Forest Retreat -Octagon

4.88 out of 5 average rating, 161 reviews

A charming two-bedroom cottage is set amidst greenery, featuring a welcoming front porch with a railing. A stone pathway leads to the entrance, and landscaping is visible around the base of the home. Large windows allow natural light to enhance the inviting exterior.

Cottage in Hebron

Welcome to The Holly at Amston Lake

5 out of 5 average rating, 11 reviews

The open-plan kitchen and living area features modern wooden cabinetry and stainless steel appliances. A large kitchen island with seating is complemented by a cozy lounge space with a floral arrangement on a patterned rug. Natural light floods the space through sliding glass doors.

Guest house in Suffield

Home Away from Home

4.91 out of 5 average rating, 405 reviews

The cozy cottage is nestled among trees, featuring a welcoming wooden deck. Reflections of the structure can be seen in the calm water of the pond, surrounded by lush greenery. A kayak is positioned in the foreground, pointing towards the entrance.

Tiny home in Orange

The Writer's Retreat: A Sweetwater Stay

4.83 out of 5 average rating, 6 reviews

Flat in Springfield

Solitude Springfield

5 out of 5 average rating, 43 reviews

A charming blue cottage is depicted, featuring a welcoming yellow front door and large windows. A stone pathway leads to the entrance, surrounded by natural landscaping. Tall pine trees offer shade, while a white picket fence encloses the property.

Home in South Hadley

Charming Riverfront Cottage

4.94 out of 5 average rating, 274 reviews

A well-maintained front yard is seen, featuring a manicured lawn and flower beds. Brick planters with blooming flowers add color. The residence showcases a brick facade with a chimney and is surrounded by greenery, providing a serene and inviting appearance.

Flat in Waterbury

Private 1 bedroom apartment in central Connecticut