Vacation rentals in Sandisfield

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Top-rated vacation rentals in Sandisfield

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

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Sep 11 – 18

G$78,584 GYD per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 14 – 21

G$22,386 GYD per night
Superhost

Home in Otis

4.94 out of 5 average rating, 128 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in The Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

Feb 11 – 18

G$76,173 GYD per night

Popular amenities for Sandisfield vacation rentals

Stay near Sandisfield's top sights

New Boston Inn7 locals recommend
Sandisfield State Forest3 locals recommend
Riiska Brook Orchard6 locals recommend

Other great vacation rentals in Sandisfield

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 reviews

Cozy Berkshires Cottage

Sep 13 – 20

G$26,100 GYD per night
Guest favorite

Home in Otis

4.94 out of 5 average rating, 144 reviews

Idyllic family retreat - spacious lake home,

May 8 – 15

G$53,497 GYD per night
Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 222 reviews

Gingerbread House Tower in the Berkshire Hills

May 13 – 20

G$59,605 GYD per night
Guest favorite

Home in Colebrook

4.99 out of 5 average rating, 200 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Dec 16 – 23

G$48,010 GYD per night
Guest favorite

Apartment in Canaan

4.98 out of 5 average rating, 102 reviews

West Main

Apr 28 – May 5

G$27,487 GYD per night
Guest favorite

Cottage in Great Barrington

4.98 out of 5 average rating, 124 reviews

Newly built cottage on working farm

Nov 7 – 14

G$24,155 GYD per night
Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 122 reviews

Cozy lakeside cottage

Nov 30 – Dec 7

G$49,905 GYD per night
Guest favorite

Farm stay in Ancram

4.95 out of 5 average rating, 257 reviews

Relaxing secluded stay with loving social animals.

Jan 15 – 22

G$32,779 GYD per night
Superhost

Home in Sandisfield

4.95 out of 5 average rating, 20 reviews

Design Cottage on a Trout River. Fly Fishing Spot!

May 14 – 21

G$34,220 GYD per night
Guest favorite

Cabin in Sandisfield

4.99 out of 5 average rating, 74 reviews

Berkshires Cabin in Woods with Mountain Views

Jun 22 – 29

G$60,456 GYD per night
Guest favorite

Home in Sandisfield

4.92 out of 5 average rating, 37 reviews

Luxury on the river@Fish Camp/Close to Tanglewood

Apr 7 – 14

G$61,266 GYD per night
Guest favorite

Home in Otis

4.82 out of 5 average rating, 56 reviews

Wintertime Oasis in the Berkshires

Jun 23 – 30

G$25,823 GYD per night

Destinations to explore