House holiday rentals in Holyoke

4.99 out of 5 average rating, 101 reviews

The living room features light blue sofas arranged around a wooden coffee table. A large flat-screen TV is mounted on the wall alongside an artwork piece, and natural light illuminates the room through a nearby window. A lamp adds additional lighting in the corner.

Home in Easthampton

3 BR Private Home~Old World Charm, Modern Touches

They don't make them like this anymore. This beautifully renovated 1800s New England Colonial is listed on the historical registry. It's a great base from which to explore all the restaurants, cultural, and outdoor activities in the beautiful Pioneer Valley. 1.5 miles from the center of Easthampton, 5 minutes to the The Williston Northampton School, and 12 minutes to Northampton/Smith College. Spread out in the full kitchen, living room, 3 large bedrooms, dining room, office, and giant yard.

4.96 out of 5 average rating, 247 reviews

Home in Southwick

Linny's - Cozy Cottage Near Congamond Lake

🌟 Welcome to Linny's - Cozy Cottage Near Congamond Lake 🌟About the Cottage: 🏠 Size: Cozy 650 sq ft house. 🚶‍♂️Just 100 steps from the lake beach Relax, recharge, and enjoy everything the Congamond Lake area has to offer from this comfortable Southwick getaway just a short walk from the water. Perfect for couples, families, weekend escapes, and lake trips, this home offers the ideal balance of relaxation, outdoor fun, and convenient access to local restaurants, boating, and attractions.

4.99 out of 5 average rating, 215 reviews

A bright and spacious studio features a cozy futon couch in a rich purple hue, paired with a wooden coffee table. A small dining area is set with a flower vase, while angled ceiling adds character. A kitchenette area is visible in the background.

Home in Williamsburg

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

A living room features a spacious leather sofa facing a large wall-mounted TV and a modern electric fireplace. A built-in shelf holds a collection of books. Soft lighting creates a comfortable ambiance, with a view of the dining area and window in the background.

4.98 out of 5 average rating, 204 reviews

Modern Comfort Meets Northampton’s Vibrant Charm

Experience the Best of Northampton! From vibrant nightlife to tranquil retreats, Northampton has something for everyone, and our newly renovated, two-bedroom duplex puts you right at the center of it all. Whether you’re catching live music, indulging in farm-to-table dining, or browsing unique local shops, every adventure is just steps away. Book your stay today and experience the perfect balance of comfort, convenience and charm in one of Northampton’s most highly rated homes!

5 out of 5 average rating, 159 reviews

A well-maintained home is situated on a gentle slope, featuring a neatly landscaped front yard with flowering plants and shrubs. An American flag is displayed by the entrance, and a gravel driveway leads to the garage below, surrounded by lush greenery.

Home in Amherst

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.

4.94 out of 5 average rating, 208 reviews

The exterior of a vintage three-story farmhouse is presented, featuring a bright yellow façade and a wrap-around porch with white railings. Lush green grass and trees surround the property, enhancing the inviting atmosphere. Multiple windows allow natural light to filter through.

Home in South Hadley

Vintage 3BR Farmhouse | Near Town + Mount Holyoke

Enjoy the charm of an 1875 farmhouse with modern comforts in this spacious 3-bedroom, 2-bath suite on the first floor! Renovated throughout, the space offers a bright living room, full kitchen, and peaceful bedrooms. Relax on the wrap-around porch or stroll to Mount Holyoke College (less than 500 meters) and Village Commons for a peaceful afternoon. Perfect for family getaways or visiting nearby colleges with Amherst and Northampton just a short 20 minute drive away.

4.97 out of 5 average rating, 348 reviews

A two-story brick house features a spacious covered porch adorned with planters and an American flag. The entrance is framed by two white doors and decorative accents. Lush greenery and small statues are placed along the walkway, enhancing the welcoming façade.

Home in Holyoke

Explore Holyoke from this charming 3 Bedroom house

This house is settled in a quiet residential neighborhood.Guests have access to the entire second floor,one flight of stairs and you're in.There are lots of windows that brighten the space,with a large dining room,office desk, and a newly renovated bathroom.The living room leads to a beautiful spacious porch over looking the park/playground.All bedrooms have comfortable matresses,lots of pillows, soft sheets,thick super soft towels. Smart TV (Netflix/hulu/sling/roku)

The exterior of a cozy guest house is presented, featuring a green facade and a welcoming entrance. A wooden deck with potted plants and decorative lights is accessible via stairs. Surrounding the house, lush greenery and garden features enhance the tranquil atmosphere.

4.94 out of 5 average rating, 285 reviews

Clean and sunny house near Smith College

Our guest house is in a quiet woodsy neighborhood 1 mile from Smith College. We are 2 miles from downtown Northampton. There is one queen bed downstairs, another queen upstairs in bedroom 2, and two twin beds in bedroom 3. There is a washer/dryer, fireplace, and back deck with gardens and woodlands. We have a new patio and hot tub right off the deck in a private area. There is a short river walk at the end of the block and a nearby trail meanders along the river.

4.89 out of 5 average rating, 1,036 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.

4.99 out of 5 average rating, 130 reviews

A charming house is visible along the riverbank, surrounded by lush greenery and blooming trees. The landscape features the calm waters of the river, reflecting the clear blue sky dotted with soft clouds, providing a scenic backdrop to the quaint property.

Home in Canton

Best River View, on Rail Trail in Collinsville!

This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

4.97 out of 5 average rating, 297 reviews

The exterior of a renovated farmhouse is surrounded by lush greenery and flowering shrubs. A stone pathway leads to the front porch, which features a pair of chairs. A barn is visible in the background, set against a backdrop of trees and hills.

Home in Russell

South Quarter House

Built in the early 1800s, our renovated farm house can accommodate families and friends comfortably. This 1600 square foot home can keep everyone together: three large bedrooms upstairs and an optional fourth downstairs. Large backyard and deck made for outside fun. Two full bathrooms, laundry, large farm table with seating for 10, and a full kitchen. Plenty of options for hiking at or near the house. (Sorry, we are not able to host weddings.)

4.95 out of 5 average rating, 111 reviews

Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Popular amenities for Holyoke house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.89 out of 5 average rating, 138 reviews

Home in Colrain

The 1770 House

5 out of 5 average rating, 58 reviews

This living area features a stone fireplace as a focal point alongside large skylights allowing natural light to fill the space. A cozy seating arrangement is present, complemented by a patterned area rug. Large glass doors open to an accessible outdoor deck, enhancing the connection to nature.

Home in Westhampton

Happy Valley getaway

4.9 out of 5 average rating, 40 reviews

A spacious living area includes a large sectional sofa in a muted tone, accented with red cushions. A glass coffee table is positioned centrally, while a decorative fireplace adds warmth. Two red and black chairs are placed against the wall, enhancing the inviting design.

Home in Springfield

Ezekiel's Palace 24th

4.86 out of 5 average rating, 37 reviews

Home in Amherst

Sweet cape near U Mass

4.93 out of 5 average rating, 15 reviews

A two-story house features light yellow siding with blue shutters around the windows. The front yard is well-maintained, showcasing green grass and neatly trimmed bushes on either side of the entrance. A concrete driveway runs alongside the home.

Home in Enfield

Enjoy New England weather and comforts of home!

4.98 out of 5 average rating, 66 reviews

Home in Chesterfield

High Field Farm

4.63 out of 5 average rating, 16 reviews

The exterior of a motel is displayed, featuring a prominent sign at the forefront. The two-story white building is complemented by surrounding greenery and well-maintained shrubbery. A red structure is visible adjacent to the main building, providing an inviting appearance.

Home in Charlemont

The lodge

4.73 out of 5 average rating, 15 reviews

Home in Vernon

RingSide Retreat-Pool, Game Room, Boxing Ring, Gym

Weekly house rentals

4.94 out of 5 average rating, 36 reviews

Luxury mid-century forest home, mins from downtown

5 out of 5 average rating, 34 reviews

A two-story cape home is situated on a lush green lawn, surrounded by trees. The exterior features a classic white façade, with a welcoming front porch and a driveway leading to a garage. Soft sunlight enhances the serene atmosphere.

Home in Easthampton

An oasis - spacious and bright

4.84 out of 5 average rating, 38 reviews

A spacious living area features a brown leather sofa and a plush area rug, complemented by a set of dining chairs around a rectangular table. Two windows allow natural light to fill the room, while a door leads to the outdoor space.

Home in Chicopee

Relax & Enjoy it all to yourself

4.98 out of 5 average rating, 98 reviews

A serene farmhouse sits amidst lush greenery, featuring a light green exterior and a charming porch. The surrounding landscape includes tall trees and dense foliage, creating a natural and tranquil setting. A chimney is visible, indicating a cozy interior.

Home in Ashfield

Magical, Rural Getaway in the Berkshires

4.98 out of 5 average rating, 40 reviews

A welcoming living space features a dark sectional sofa positioned near a light-colored coffee table. An elegant fireplace with a decorative mantle is centered on the wall, complemented by a mounted television above. Natural light filters through sheer curtains, enhancing the calming atmosphere.

Home in Springfield

Nana's house

5 out of 5 average rating, 10 reviews

Home in East Longmeadow

Warm 3 BR house w/ fenced yard close to everything

The entrance features a covered porch with white railings, providing a welcoming pathway to the door. A potted plant with pink flowers is situated near the base of the stairs, adding a touch of greenery to the inviting entrance.

4.93 out of 5 average rating, 92 reviews

The Walnut Apartment

4.83 out of 5 average rating, 71 reviews

A living area features a navy sofa paired with wooden chairs around a circular table. A stone fireplace creates a focal point, with a clock affixed above. The kitchen is visible in the background, showcasing stainless steel appliances and wooden cabinetry.

Home in Agawam

Home near Six Flags/ hot tub

Private house rentals

4.88 out of 5 average rating, 52 reviews

The master bedroom features a spacious bed with a light-colored duvet. Natural light enters through three windows, accented by flowing white curtains. A large mirror and a decorative plant add touches of style, while a soft rug lies on the polished floor.

Home in Springfield

Cozy Hall of Fame Gem

4.98 out of 5 average rating, 43 reviews

A cozy bedroom features a queen-size bed, dressed in soft white linens and a teal accent throw. A piece of wall art adds character above the bed. Natural light filters in through a window, complemented by light curtains. A wooden dresser provides storage space.

Home in Enfield

Nest&Rest Escape

4.98 out of 5 average rating, 94 reviews

A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.

Home in Ashfield

An 18th century farmhouse

5 out of 5 average rating, 26 reviews

A serene lakehouse is surrounded by lush greenery, reflecting beautifully in the calm lake below. The structure features large windows and a deck extending to the water, enhancing the natural landscape. An American flag stands nearby, complementing the peaceful atmosphere.

Home in Becket

Private Lakehouse in the heart of the Berkshires

4.86 out of 5 average rating, 86 reviews

A modern single-story home is framed by a vibrant red bush and manicured lawn under an orange and pink sunset sky. The house features a chimney, inviting entryway, and accessible garage, creating a welcoming exterior.

Home in Blandford

Relaxing Home nestled in Rural Hilltown

5 out of 5 average rating, 9 reviews

Home in Granby

Lake House Retreat Granby CT

4.94 out of 5 average rating, 36 reviews

The exterior of the home is bathed in soft evening light, highlighting the warm wood tones of the siding. Cozy outdoor seating is arranged under string lights in the backyard, creating an inviting atmosphere. Lush greenery and ferns surround the area, enhancing the sense of tranquility.

Home in Amherst

Amherst Treehouse