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Vacation rentals in Otis

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Top-rated vacation rentals in Otis

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

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Chalet in Otis

4.94 out of 5 average rating, 380 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

Treehouse in Tyringham

5 out of 5 average rating, 268 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.

Home in Otis

4.94 out of 5 average rating, 142 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)

Rental unit in Otis

4.85 out of 5 average rating, 104 reviews

Fall Oasis in the Berkshires

Beautiful, centrally located home in Otis with seasonal water views of the reservoir! Just a few minutes drive from Otis ridge ski resort and the local lakeside beach for seasonal activities. This home is located next door to the only eat in Restaurant/Bar in town and even has a private trail that leads to this restaurant, Katies country store and boat Launch on the Otis reservoir! That same trail is also ride on snowmobile access for snowmobilers and enduro riders/mountain bikers and hikers.

Home in Chester

4.96 out of 5 average rating, 335 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Guesthouse in Lenox

4.92 out of 5 average rating, 194 reviews

Modern Barn with Loft at House on Golden Hill

Featuring 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

Home in Monterey

4.92 out of 5 average rating, 129 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.

Home in Otis

4.92 out of 5 average rating, 146 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.

Cottage in Becket

4.94 out of 5 average rating, 267 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)

Home in Otis

4.97 out of 5 average rating, 104 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Home in Great Barrington

4.97 out of 5 average rating, 240 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.

Home in Otis

4.86 out of 5 average rating, 174 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.

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Popular amenities for Otis vacation rentals

Free parking on premises

Air conditioning

Stay near Otis's top sights

Otis Ridge25 locals recommend

Katie's Country Store and Takeout18 locals recommend

Fratelli's Restaurant & Pizza14 locals recommend

Sherwood Shoppe15 locals recommend

Knox Trail Inn14 locals recommend

Ashintully Gardens13 locals recommend

Other great vacation rentals in Otis

Chalet in Otis

4.9 out of 5 average rating, 52 reviews

Thrill & Chill: Ski & Sauna in Winter Wonderland

Home in Otis

4.91 out of 5 average rating, 11 reviews

Berkshires Oasis Retreat: Art Meets Nature

Home in Becket

4.95 out of 5 average rating, 65 reviews

Nerd Preservation Sanctuary

Home in Becket

5 out of 5 average rating, 13 reviews

Berkshires Lakefront Retreat

Home in Otis

4.81 out of 5 average rating, 37 reviews

Private Berkshires Home On 5+ Acres, Rustic & Chic

Home in Otis

4.92 out of 5 average rating, 13 reviews

Spacious Lake Front Home

Home in Becket

5 out of 5 average rating, 29 reviews

Berkshires Lakefront Stylish Retreat w/Gameroom

Home in Otis

4.96 out of 5 average rating, 24 reviews

Home In Otis

Quick stats about vacation rentals in Otis

Total rentals
90 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool

Frequently Asked Questions

Are there Otis vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Otis, available on Airbnb. Make a splash and soak up the sun in style!
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 house rentals in Otis have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Otis. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Otis have wifi?
Absolutely! We offer over 10 cabin 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 20 homes with a bbq area, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do cabin rentals in Otis have a bbq area?
Absolutely! We offer over 20 cabin 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.
How much does it cost to stay in house rentals in Otis?
Experience the best of Otis with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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