Vacation rentals in Monroe

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Top-rated vacation rentals in Monroe

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Guest favorite

Apartment in Shelburne Falls

4.91 out of 5 average rating, 239 reviews

Soaring 2-level loft w/ views in heart of downtown

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Top guest favorite

A dedicated laundry area is visible, featuring stacked white washer and dryer units with sleek silver accents. Above, light wood cabinetry provides additional storage. A light-colored, tiled floor complements the appliances, creating a tidy and functional space.

Cabin in Savoy

4.97 out of 5 average rating, 218 reviews

The Camp - hiking trails right outside your door

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

Top guest favorite

A red carriage house is set against a backdrop of mountains and blue skies. White Adirondack chairs circle a stone fire pit, while a picnic table and umbrella provide additional outdoor seating. Lush greenery surrounds the area, creating a serene environment.

Guesthouse in North Adams

5 out of 5 average rating, 271 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

Superhost

The screened porch features a stone fireplace with a warm fire, creating a cozy ambiance. A stack of firewood is neatly arranged beside it. Simple wooden rocking and metal chairs offer seating, with wooden flooring that enhances the rustic feel of the space.

Cabin in Clarksburg

4.9 out of 5 average rating, 279 reviews

Mountain Cottage Spectacular Views

This lovely cottage sits on 90 acres featuring gardens, fruit groves, forest, and the Hoosic River. Spectacular views of Mt Greylock. Truly an idyllic location, the perfect retreat for a lover of the outdoors but also close to cultural offerings. Less than 10 minutes to downtown North Adams and Mass MOCA. Williamstown and the Clark Art Institute are nearby as well. Plenty of long or short hikes, scenic walks and bike rides as well as local restaurants and shops that are easily accessible.

Guest favorite

A spacious lodge features a prominent stone chimney and large windows that invite natural light. Multiple decks offer outdoor seating options, while lush greenery and manicured lawn surround the structure, creating an inviting exterior against a colorful sunset sky.

Place to stay in North Adams

4.93 out of 5 average rating, 155 reviews

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Top guest favorite

The entrance of a light green house is shown, featuring a welcoming door with multiple glass panes. A wooden welcome mat lies at the foot of the door, while a pathway leads through a well-maintained grassy area beside it.

Guest suite in Williamstown

4.96 out of 5 average rating, 237 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Guest favorite

A night sky displays a gradient of purple and dark blue tones, with stars scattered across the expanse. Silhouettes of power lines extend from the foreground into the distance, contrasting against the celestial backdrop.

Camper/RV in Guilford

4.93 out of 5 average rating, 137 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Guest favorite

A river flows over smooth, large stones, creating a gentle waterfall. Lush trees frame the scene, with a distant view of charming buildings along the riverbank. The sky is partly cloudy, complementing the serene natural surroundings.

Cottage in Monroe

4.87 out of 5 average rating, 132 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 charming blue building showcases a welcoming exterior with white columns and a well-kept porch. Bright orange daylilies bloom in the foreground, complementing the lush green landscape. The gravel path leads to the entrance, framed by greenery and trees.

Apartment in Stamford

4.87 out of 5 average rating, 312 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Escape to our cozy apartment in picturesque Southern Vermont! Featuring a comfortable bedroom, a well-equipped kitchenette, a private bathroom, and a charming dining area, this space has everything you need for a relaxing stay. Enjoy the perfect blend of tranquility and easy access—just a scenic 10-minute drive brings you to North Adams, MA, home to Mass MoCA, MCLA, and plenty of dining and shopping. Book now for the ideal balance of serenity and convenience!

Top guest favorite

Home in North Adams

4.99 out of 5 average rating, 107 reviews

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Guest favorite

The exterior of a dark wooden building is shown, with large windows reflecting the evening sky. A soft gradient of colors appears in the clouds, while a faint contrail stretches across the sky, framed by surrounding trees.

Loft in Heath

4.86 out of 5 average rating, 115 reviews

Cozy loft apartment in adventurers paradise

Relax in our uniquely decorated loft apartment. This location is a privately secluded homestead, bordering the Maitland Memorial Forest. Just minutes from all of your favorite outdoor adventures! We are 10 mins from the Berkshire East Mountain Resort and the Deerfield river. We have bike storage and a great repair area. Amenities: Full kitchen and bath.

Top guest favorite

The image shows a private outdoor Finnish sauna featuring warm wooden walls and a glass door. An efficient wood stove is visible, providing heat, along with a small wooden bench for comfort. A soft mat covers the floor, creating a tranquil atmosphere.

Apartment in North Adams

4.97 out of 5 average rating, 556 reviews

Steps to MoCA: 2bd + SAUNA!

A large and private 2 bedroom apt at the Small Mansion of Chase Hill, 3 mins by walk to Mass MoCA. 10 mins drive to Williams College, Clark. 5 mins walk to downtown’s restaurants. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat YOUR STAY HERE ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!