House vacation rentals in Otis

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Top-rated house rentals in Otis

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Guest favourite

Home in Lee

4.89 out of 5 average rating, 236 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. 30 – Oct. 7

$211 CAD per night

Guest favourite

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.

Nov. 22 – 29

$584 CAD 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)

Sep. 3 – 10

$595 CAD per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 114 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Mar. 7 – 14

$156 CAD per night

Guest favourite

Home in Becket

4.87 out of 5 average rating, 289 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Sep. 4 – 11

$349 CAD per night

Guest favourite

Home in Chester

4.96 out of 5 average rating, 312 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!

Oct. 14 – 21

$293 CAD per night

Guest favourite

Home in Williamsburg

4.99 out of 5 average rating, 158 reviews

Hilltown Studio

Stunning 2nd floor studio (limited kitchenette with easy to prepare Breakfast foods provided) close to Northampton, Smith and the Five Colleges, scenic drive to the Berkshires, one mile to the Snow Farm and just minutes to Valley View Farm. Lovely space & private deck overlooking perennial gardens & wildlife wandering by. Perfect stop when traveling through Western Mass, touring local colleges or a trip to enjoy the music, museums and restaurants in the Pioneer Valley and Berkshires.

Nov. 2 – 9

$178 CAD per night

Guest favourite

Home in Lee

5.0 out of 5 average rating, 231 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

Apr. 21 – 28

$526 CAD per night

Guest favourite

Home in Monterey

4.93 out of 5 average rating, 116 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. 6 – 13

$224 CAD per night

Guest favourite

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.

Nov. 17 – 24

$405 CAD per night

Guest favourite

Home in Great Barrington

4.96 out of 5 average rating, 214 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.

Mar. 26 – Apr. 2

$1,200 CAD per night

Guest favourite

Home in Southwick

4.99 out of 5 average rating, 182 reviews

Linny's Lakeview Cottage

Linny's lakeview cottage is updated with beautiful hardwood floors. The kitchen is finished in white shaker cabinets, granite counter tops & new ss appliances. The counter joins the kitchen/living room & comfortably sits 6. This is a renovated 650 sq ft home. Access our online guidebook (a few day before your stay) for; house rules, local attractions, maps, and more, ensuring you make the most of your stay.

Aug. 21 – 28

$277 CAD per night