Vacation rentals in Otis

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Top-rated vacation rentals in Otis

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Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 347 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

Oct 27 – Nov 3

ﺩ.ﺇ1,483 per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 255 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!

Oct 14 – 21

ﺩ.ﺇ363 per night

Guest favorite

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

Sep 2 – 9

ﺩ.ﺇ2,105 per night

Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 225 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Jul 21 – 28

ﺩ.ﺇ1,137 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)

Oct 16 – 23

ﺩ.ﺇ1,352 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.

Jan 1 – 8

ﺩ.ﺇ447 per night

Guest favorite

Home in Monterey

4.93 out of 5 average rating, 115 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

Family-friendly rustic modern getaway set on 4 acres in the beautiful Berkshires. Escape the city and work using our fiber internet, or just come relax and read a book by the fire. Spend time in the great outdoors skiing at Butternut, hiking at Bob's Way or taking in a cultural event at Tanglewood or Jacobs Pillow. 15 minutes to Great Barrington, Lee and Lenox. 5 minutes to Otis Ridge ski, 15 minutes to Butternut and 25 to Catamount there is always something to do.

Sep 9 – 16

ﺩ.ﺇ676 per night

Guest favorite

Home in Otis

4.92 out of 5 average rating, 131 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Aug 4 – 11

ﺩ.ﺇ1,045 per night

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

Jan 11 – 18

ﺩ.ﺇ694 per night

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 212 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Feb 6 – 13

ﺩ.ﺇ2,630 per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 275 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 6 – 13

ﺩ.ﺇ539 per night

Guest favorite

Home in Otis

4.85 out of 5 average rating, 161 reviews

The Meadows House @ Otis Ridge w/ 7-person hot tub

Relax in a beautiful mountain setting at this 4-season ski house within walking distance of the slopes at Otis Ridge Ski Area (the best ski area south of the Vermont border). In fact, the back-yard (actually a meadow full of wildlife and flowers) used to be part of the ski area and there are still remnants of the rope-tow on the edge of the property. The long-range views off the back porch are fantastic.

Jun 9 – 16

ﺩ.ﺇ920 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Otis vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Otis's top sights

Knox Trail Inn14 locals recommend

Katie's Country Store and Takeout18 locals recommend

Farmington River Diner9 locals recommend

Becket Quarry9 locals recommend

Fratelli's Restaurant & Pizza15 locals recommend

Grouse House Restaurant & Inn10 locals recommend

Other great vacation rentals in Otis

Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Sep 26 – Oct 3

ﺩ.ﺇ458 per night

Guest favorite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 reviews

Sunny Berkshire Studio Apartment

Jan 1 – 8

ﺩ.ﺇ424 per night

Guest favorite

Home in Chester

4.96 out of 5 average rating, 310 reviews

Riverfront Getaway

Nov 26 – Dec 3

ﺩ.ﺇ672 per night

Guest favorite

Home in Lee

4.9 out of 5 average rating, 202 reviews

1817 Berkshire Farmhouse- Close to Everything.

Apr 24 – May 1

ﺩ.ﺇ569 per night

Guest favorite

Apartment in Great Barrington

4.95 out of 5 average rating, 317 reviews

Private En Suite in Beautiful Victorian

Mar 15 – 22

ﺩ.ﺇ406 per night

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 124 reviews

Cozy lakeside cottage

Nov 19 – 26

ﺩ.ﺇ1,006 per night

Guest favorite

Home in Otis

4.83 out of 5 average rating, 58 reviews

Springtime Oasis in the Berkshires!

Jun 7 – 14

ﺩ.ﺇ399 per night

Guest favorite

Apartment in Otis

4.98 out of 5 average rating, 60 reviews

Enjoy every season the Berkshires have to offer.

Sep 17 – 24

ﺩ.ﺇ632 per night

Show all

Quick stats about vacation rentals in Otis

Total rentals
90 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees

Frequently Asked Questions

Do house rentals in Otis have a gym?
Absolutely! We offer over 10 house rentals with a gym in Otis. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Otis?
Yes! Work meets play with ease at over 50 vacation rentals in Otis featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cabin rentals in Otis have air conditioning?
Absolutely! We offer over 10 cabin rentals with air conditioning in Otis. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Otis have wifi?
Absolutely! We offer over 50 house rentals with wifi in Otis. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Otis?
Four-legged friends are welcome in Otis. Choose from more than 30 vacation rentals for guests traveling with pets.
What are the most popular amenities for Cabin Rentals in Otis?
Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with air conditioning, over 20 homes with a bbq area, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Otis have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Otis. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Otis?
Otis has more than 80 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Otis

Top-rated vacation rentals in Otis

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Otis vacation rentals

Stay near Otis's top sights

Other great vacation rentals in Otis

Home in Lee

Apartment in Sandisfield

Home in Chester

Home in Lee

Apartment in Great Barrington

Cottage in Becket

Home in Otis

Apartment in Otis

Quick stats about vacation rentals in Otis

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Otis have a gym?

Are there vacation rentals with a dedicated workspace in Otis?

Do cabin rentals in Otis have air conditioning?

Do house rentals in Otis have wifi?

Are there pet-friendly vacation rentals in Otis?

What are the most popular amenities for Cabin Rentals in Otis?

Do house rentals in Otis have a bbq area?

Are there family-friendly vacation rentals in Otis?

Destinations to explore