Holiday rentals in Monroe

Guest house in Marlboro Township

4.97 out of 5 average rating, 160 reviews

Refined, serene and like no other, Marlboro, VT.

Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

4.97 out of 5 average rating, 219 reviews

Cabin in Savoy

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.

4.9 out of 5 average rating, 281 reviews

Cabin in Clarksburg

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.

4.99 out of 5 average rating, 158 reviews

Flat in Charlemont

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

4.98 out of 5 average rating, 561 reviews

Flat in Shelburne Falls

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

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.

Guest suite in Williamstown

4.96 out of 5 average rating, 239 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.

4.88 out of 5 average rating, 164 reviews

Tiny home in Brattleboro

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

4.87 out of 5 average rating, 134 reviews

Cottage in Monroe

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!

4.87 out of 5 average rating, 313 reviews

Flat in Stamford

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!

4.92 out of 5 average rating, 109 reviews

Flat in North Adams

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

Experience North Adams with unbeatable convenience! This centrally located apartment puts your whole group just a short walk or bike ride away from Mass MoCA, the farmer’s market, and the shops and restaurants on Main Street. Enjoy stress-free access to all the local attractions—no parking hassles, just easy, enjoyable days exploring the best of North Adams. Perfect for your next Mass MoCA event or weekend getaway!

4.86 out of 5 average rating, 117 reviews

Loft in Heath

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.

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Popular amenities for Monroe holiday rentals

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Free parking on premises

Air conditioning

Other great holiday rentals in Monroe

4.9 out of 5 average rating, 10 reviews

Cabin in Stamford

La Cabañita - The Little Cabin

PatriciaRating, 5 stars1 day ago

We were looking for a quiet get away in a log cabin and this was the perfect match. We absolutely loved the cabin! It was set up for a cozy retreat for a couple or a family, nestled in the mountains but with all of the modern conveniences : tv, wifi, games, complete kitchen (no microwave), screened in porch that we really enjoyed, and comfortable beds and bathroom. The cabin was very clean and well appointed and even included a crate for your dog if needed. The nearest General Store is 8 to 10 miles away so be prepared to bring what food you need. We found the store in Readsboro offered a yummy selection of made to order sandwiches if you want to check out the area. Our host was very helpful when we had questions and responded quickly. We would love to come here again in the fall to enjoy the foliage.

4.83 out of 5 average rating, 60 reviews

Flat in North Adams

Walnut Way basement apartment

BenRating, 5 stars1 month ago

It was bigger in person! Easy check in, check out. Megan was easy to communicate with.

5 out of 5 average rating, 62 reviews

Home in Whitingham

2.5mi from the lake! Fire pit, arcade, yard games!

JohnRating, 5 stars6 days ago

My 2nd time staying here. Always amazing. Check out Sprague and Sons Sugar House. Home baked breads, Maple Products, Cookies absolutely delicious. Even Maple Ice Cream and home baked Chocolate Chip Cookie with Maple Ice Cream sandwiches. The home is absolutely gorgeous and has Everything you need or want. Great stay. Eric is so helpful and welcoming. Very responsive to messages any time you need him. Thanks for an Incredible Experience. We hope to be back again soon.

5 out of 5 average rating, 4 reviews

Cabin in Florida

Lux Berkshires Mtn Cabin: Near MassMOCA & Williams

JordanRating, 5 stars5 days ago

We loved staying at Tito's cabin. The land is beautiful and the space is well taken care of. It's a cozy, restful cabin that's off the beaten path and has everything you need for a weekend away.

4.89 out of 5 average rating, 28 reviews

Apartment in North Adams

Downtown Condo - walk to MoCA

RuthRating, 5 stars2 weeks ago

My husband and I loved our stay at Jo Anne’s place, it was quite,clean private, easy access to parking and very affordable . Stocked with the necessities.

4.92 out of 5 average rating, 50 reviews

Home in Guilford

Vermont Mirror House

GeorgeRating, 5 stars1 week ago

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

5 out of 5 average rating, 10 reviews

Flat in Whitingham

Vermont Lake Whitingham Mount Snow Area Apartment

EvaRating, 5 stars4 days ago

Honestly, I wish I could give this place more than five stars. How it was still available (we booked pretty last-minute) is beyond me, this should be fully booked at all times. The apartment is incredibly cosy, and so nicely furnished. The attention to detail is incredible, from the wash bassinet and the shower curtains in the bathroom, to the bedding and the curtains, it's all just lovely. Amy and her co-host Connor are super friendly, respond fast and are just comfortable to be around. They even went through extra effort to make space for our son's pack and play, and put out some blocks and cardboard books. And we were given some fresh, homemade cupcakes too! It's good to be aware of the fact that it's not a very large space but it has everything you'll need, from a microwave to a lovely little bath. If we ever come back to this region in the U.S. we'd definitely book this again. Honestly, I cannot recommend it enough.