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, 349 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

Dec 9 – 16

G$78,223 GYD per night

Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 228 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.

Aug 30 – Sep 6

G$68,849 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)

Jan 9 – 16

G$76,300 GYD per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 258 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.

Dec 18 – 25

G$25,376 GYD per night

Guest favorite

Home in Chester

4.96 out of 5 average rating, 310 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!

Jul 28 – Aug 4

G$38,123 GYD 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.

Apr 5 – 12

G$59,305 GYD per night

Guest favorite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 reviews

Sunny Berkshire Studio Apartment

Sunny many windowed studio apartment attached at west end of the main house. Self contained with kitchen and bathroom. Plus addition sleeping area (attached bedroom). Studio and bedroom have full size beds Studio also has narrow twin futon. 1 mile long gravel road for a "walk out the door and go" wake up morning hike. State forest is across from house, along Bosworth Road and along Rt 57. Long Term Guests welcome. $5/guest after 2. PET FEE: $25/stay

Feb 21 – 28

G$24,087 GYD per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 280 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 8 – 15

G$30,538 GYD 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.

Oct 29 – Nov 5

G$149,304 GYD per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Sep 7 – 14

G$24,546 GYD per night

Guest favorite

Home in Otis

4.85 out of 5 average rating, 162 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.

Nov 9 – 16

G$51,140 GYD per night

Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 706 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Apr 7 – 14

G$33,731 GYD 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 Monterey

4.93 out of 5 average rating, 116 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

Oct 2 – 9

G$38,054 GYD per night

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

Jul 29 – Aug 5

G$40,871 GYD per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 reviews

Cozy Berkshires Cottage

Sep 22 – 29

G$25,980 GYD per night

Guest favorite

Guesthouse in Northampton

5.0 out of 5 average rating, 272 reviews

Mill River Cottage (pet friendly!)

Mar 24 – 31

G$25,191 GYD per night

Guest favorite

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Feb 8 – 15

G$71,915 GYD per night

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 238 reviews

Sunny, light filled loft in 1873 Colonial

Mar 3 – 10

G$24,811 GYD per night

Guest favorite

Home in Otis

4.83 out of 5 average rating, 59 reviews

Springtime Oasis in the Berkshires!

Jun 3 – 10

G$22,876 GYD per night

Guest favorite

Apartment in Otis

4.98 out of 5 average rating, 60 reviews

Enjoy every season the Berkshires have to offer.

May 17 – 24

G$32,329 GYD 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
G$12,509 GYD 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 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 House Rentals in Otis?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with a gym, over 40 homes with a bbq area, over 30 homes with air conditioning, over 50 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 Monterey

Cottage in Becket

Home in Lee

Guesthouse in Northampton

Home in Becket

Apartment in Plainfield

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 cabin rentals in Otis have wifi?

Are there pet-friendly vacation rentals in Otis?

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

Do house rentals in Otis have a bbq area?

Are there family-friendly vacation rentals in Otis?

Destinations to explore