Vacation rentals with a patio in Charlemont

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Top-rated patio rentals in Charlemont

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Guest favorite

Chalet in Charlemont

4.98 out of 5 average rating, 42 reviews

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

Oct 18 – 25

G$95,813 GYD per night

Guest favorite

Place to stay in North Adams

4.93 out of 5 average rating, 115 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.

Aug 12 – 19

G$138,036 GYD per night

Guest favorite

Cottage in Deerfield

4.97 out of 5 average rating, 88 reviews

Dreamy Guesthouse: sauna and private deck

You will feel like you're deep in the country while being close to everything on this 11-acre homestead, surrounded by woods. Featuring an infrared sauna, breezy porch, and firepit, this private guesthouse (next to our residence) is a 15-min walk to Deerfield Academy, Bement, Eaglebrook, and Historic Deerfield; a short drive to all five colleges; and less than three miles from award-winning Treehouse Brewery. Halfway between Brattleboro and Northampton, this is the perfect valley spot.

Dec 14 – 21

G$33,388 GYD per night

Guest favorite

Home in Adams

4.91 out of 5 average rating, 68 reviews

Mountain View Hideaway

Welcome to the Hideaway! This 800sqft home is located on a small hill with a beautiful direct view of Mount Greylock. This amazing home is perfect for anyone who's looking to explore the Berkshires by day and come back to a tranquil home by evening. This small but mighty house has a full kitchen, very comfortable lounging couch, quiet bedroom with an adjacent office area, full bathroom with a washer and dryer and a front and back yard. Everyone is welcomed to enjoy this gem of a home!

Feb 18 – 25

G$24,416 GYD per night

Guest favorite

Cottage in Newfane

4.99 out of 5 average rating, 177 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Aug 20 – 27

G$32,436 GYD per night

Guest favorite

Treehouse in Guilford

4.99 out of 5 average rating, 84 reviews

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Oct 14 – 21

G$26,496 GYD per night

Guest favorite

Cottage in Orange

4.94 out of 5 average rating, 132 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Jan 6 – 13

G$25,149 GYD per night

Guest favorite

Cottage in Monroe

4.89 out of 5 average rating, 83 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!

Jun 11 – 18

G$26,186 GYD per night

Guest favorite

Apartment in Charlemont

4.92 out of 5 average rating, 65 reviews

Stylish two bedroom apartment in Charlemont

Located in the heart of Charlemont, just minutes away from skiing and biking at Berkshire East, as well as white water rafting and fishing on Deerfield River. This newly renovated, spacious apartment is perfect for your home base for adventure or relaxation in the hills of Western Mass. It is located over Wells Provisions, a highly regarded cafe and market serving Creole and Cajun food made with local ingredients and some of the best coffee and espresso around.

Apr 1 – 8

G$53,817 GYD per night

Guest favorite

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 127 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

Dec 4 – 11

G$19,402 GYD per night

Guest favorite

Apartment in Charlemont

5.0 out of 5 average rating, 128 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a short walk to Berkshire East and the Deerfield River. You’ll love our large yard, the brook, private picnic area, enjoy an outdoor fire. This town awaits fun-filled adventures biking, skiing, leaf peeping, fishing , tubing, whitewater rafting, snowmobiling. We reside at the single family home on property and we’re excited to share our place with you.

Jun 4 – 11

G$46,952 GYD per night

Guest favorite

Cabin in Charlemont

4.9 out of 5 average rating, 105 reviews

Mountain View Cabin House

Forget your worries in this spacious and serene space. Steps away to Ski/mountain biking Resort, Deerfield River fly fishing all year long. Berkshire East Mountain Resort and Zoar Out Door just two minutes away. Mohawk Trail State Forest and Avery's General Store right in the corner. Come and enjoy Nature, Sports and Peace of Mind!!!

Sep 1 – 8

G$55,955 GYD per night