Vacation rentals in Mount Holyoke

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Top-rated vacation rentals in Mount Holyoke

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Superhost

A charming two-story white house is surrounded by greenery, featuring a welcoming front porch with rocking chairs. The structure showcases large windows and a shingled roof, with a pathway leading to the entrance. The tranquil setting is complemented by the rustic stone bench in front.

Home in Litchfield County

4.8 out of 5 average rating, 10 reviews

Charming home ready for fun and/or relaxation!

Enjoy our peaceful (pet friendly) home, at the end of a dead-end road & just a short walk to the center of Norfolk. Great for friends and/or family visits. Board games & puzzles inside; lawn games & fire pit outside. Front & back decks, including screened-in porch, are perfect for relaxing. Access great cafes, shops & cultural delights in Norfolk. The nearby Ellen Battell Stoeckel Estate hosts Yale's Summer Chamber Music Concert series. It’s a home, not a hotel. But, we think you’ll love it!

Guest favorite

A private dock extends into the calm lake, featuring a sliding board and a set of stairs leading into the water. A rustic playhouse sits nearby, complemented by a wooden bench. Colorful Adirondack chairs surround the area, offering serene views of the surrounding nature.

Cottage in Becket

4.94 out of 5 average rating, 197 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Guest favorite

A wooden dock extends over a tranquil lake, surrounded by lush trees and colorful foliage. The water reflects the blue sky and fluffy white clouds, creating a peaceful outdoor setting. This image highlights the natural beauty and serenity of the area.

Cottage in Becket

4.78 out of 5 average rating, 163 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

Tranquil 3-Acre Getaway in Becket, MA Escape to our charming 1,504 sq. ft. retreat on 3 acres in a private lake community. This historic home offers timeless appeal with a spacious 350 sq. ft. deck surrounded by lush trees. Take a 5-minute stroll to the lake. Key Features: Expansive Deck: Ideal for outdoor dining and relaxation. Lake Access: Enjoy water sports steps away. Modern Amenities: Features HDTV for streaming. Book your Becket escape today and experience the beauty of the Berkshires!

Guest favorite

A hammock is suspended between two trees, offering a serene view of Sadawga Lake. Lush greenery surrounds the area, with gentle blue skies and soft clouds reflected in the water. The grass below is well-maintained, creating a peaceful spot for relaxation.

Tiny home in Whitingham

4.91 out of 5 average rating, 99 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Guest favorite

The living area features hardwood floors and large windows that allow natural light to fill the space. A staircase with wooden railings leads to the upper level. Seating includes a gray sofa, two accent chairs, and a coffee table, complemented by an entertainment center with a television.

Home in Becket

4.88 out of 5 average rating, 339 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Top guest favorite

A grassy yard is framed by tall trees, creating a serene natural setting. A circular stone fire pit is surrounded by bright red chairs, offering a cozy spot for gatherings. A spacious deck with seating is visible adjacent to the house, providing an ideal area for relaxation.

Home in North Adams

5 out of 5 average rating, 109 reviews

Berkshires Retreat! in the woods, yet in town!

We are happy to share our piece of heaven in the Berkshires! Newly renovated 4-bedroom 2-1/2-bathroom vacation rental nested in 2.7 acres of woods, yet conveniently located in the city of North Adams. A 5 minute walk from Windsor Lake, a 15 minute walk to MASS MoCA, and a close drive to many restaurants. The house is kid friendly, basketball hoop, soccer goal, and games. We are close to ski resorts, as well hiking and biking trails, including Mount Greylock. PET FEE. PERMISSION NEEDED.

Guest favorite

A wooden deck extends towards a serene lake, framed by trees. Two lounge chairs are positioned for relaxation, alongside a grill. An American flag flutters in the gentle breeze, while the tranquil water reflects sunlight, enhancing the natural ambiance.

Home in Otis

4.9 out of 5 average rating, 51 reviews

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Guest favorite

Cottage in Monroe

4.9 out of 5 average rating, 126 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Guest favorite

A spacious bedroom features a green wooden bed dressed in white linen, flanked by large windows with sliding doors leading to a serene outdoor view. A comfortable armchair and a small side table are positioned nearby, adding to the cozy ambiance.

Home in Otis

4.92 out of 5 average rating, 153 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Superhost

Apartment in Chester

4.77 out of 5 average rating, 197 reviews

Quiet getaway in the Berkshires

Very nice quite place Two floors must climb stairs 3 bedrooms very large master Fully equipped kitchen Two full baths and laundry area Deck off the kitchen with fire pit in the back yard Lots of hiking and skiing in and around the area or stay and relax Carm’s diner for a great Breakfast Chester Common Table for dinner or The Blue Note Cafe for Pizza and a drink or Call for some takeout and a convenient store for anything you forgot

Top guest favorite

Two wooden Adirondack chairs face a small fire pit, surrounded by a serene wooded area. A picnic table is positioned nearby, with a stack of firewood to the side. The Green River flows gently in the background, framed by vibrant greenery.

Apartment in Williamstown

5 out of 5 average rating, 125 reviews

Downtown | Waterfront | Walk to Shops

★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.

Top guest favorite

Home in Brimfield

4.94 out of 5 average rating, 164 reviews

Brimfield Lakeside Home Away from Home

Renovated Brimfield Lakeside Home: minutes to downtown Brimfield & Sturbridge offers two bedrooms plus additional upstairs loft sleeping area, one bath & sleeps six. We are a year round property located in a quiet cove on beautiful Little Alum Pond in Brimfield, Massachusetts. Extremely tranquil setting, yet plenty of great restaurants and shopping are just minutes away.