Vacation rentals in Hinsdale

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Top-rated vacation rentals in Hinsdale

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Sep 13 – 20

R2,360 ZAR per night
Guest favorite

Cabin in Savoy

4.98 out of 5 average rating, 184 reviews

The Camp - 20 Minutes to Berkshire East!

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.

Aug 25 – Sep 1

R2,160 ZAR per night
Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 257 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

May 5 – 12

R2,305 ZAR per night

Popular amenities for Hinsdale vacation rentals

Stay near Hinsdale's top sights

Ozzie's Steak & Eggs16 locals recommend
Bas Ridge Country Club8 locals recommend
Holiday Brook Farm3 locals recommend

Other great vacation rentals in Hinsdale

Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Jun 16 – 23

R1,867 ZAR per night
Guest favorite

Cabin in Cummington

4.98 out of 5 average rating, 159 reviews

Just Be Cabin

Sep 22 – 29

R1,274 ZAR per night
Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 248 reviews

Wildlife Lakeside Cottage

Feb 4 – 11

R5,174 ZAR per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 224 reviews

Berkshire Mountain retreat with Urban eco-luxuries

Mar 19 – 26

R6,185 ZAR per night
Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

Oct 17 – 24

R3,579 ZAR per night
Guest favorite

Cabin in Hinsdale

4.9 out of 5 average rating, 69 reviews

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere

Apr 4 – 11

R4,140 ZAR per night
Guest favorite

Home in Hinsdale

4.94 out of 5 average rating, 49 reviews

Berkshire Lake Retreat

Nov 30 – Dec 7

R3,831 ZAR per night
Superhost

Cabin in Hinsdale

4.97 out of 5 average rating, 31 reviews

Relaxing Berkshire cabin on Lake Ashmere

Mar 2 – 9

R4,503 ZAR per night
Guest favorite

Cottage in Hinsdale

4.97 out of 5 average rating, 68 reviews

Berkshires - Charming Lakefront Cottage

Jan 22 – 29

R7,000 ZAR per night
Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 24 reviews

Comfortable Pittsfield Loft

Feb 1 – 8

R1,421 ZAR per night
Guest favorite

Apartment in Pittsfield

5.0 out of 5 average rating, 41 reviews

Simply off North

Sep 23 – 30

R1,575 ZAR per night
Superhost

Apartment in Pittsfield

4.81 out of 5 average rating, 16 reviews

Cozy Studio Apt in Downtown Victorian

Apr 17 – 24

R1,511 ZAR per night

Destinations to explore