Condo vacation rentals in The Berkshires

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Top-rated condo rentals in The Berkshires

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

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Guest favorite

Condo in Poughkeepsie

4.97 out of 5 average rating, 224 reviews

Spacious and stylish entire one bedroom apartment.

Enjoy a stylish experience at this centrally-located one bedroom apartment in Poughkeepsie. Apt is located in a quiet Victorian townhouse on the 3rd floor. Entire rental unit, Parking is included for one vehicle. Located downtown. Walking distance to: Post Office, Courts, County Bldgs, Police Station, City Hall, Nesheiwat Convention Center (fka Civic Center), Poughkeepsie Grand Hotel, Walkway Over The Hudson, Bardavon Opera House, The Academy, train station, waterfront, bus depot, and more.

Jul 12 – 19

G$28,908 GYD per night

Guest favorite

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Jun 6 – 13

G$43,180 GYD per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 133 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Jul 27 – Aug 3

G$22,934 GYD per night

Guest favorite

Condo in Hunter

4.97 out of 5 average rating, 428 reviews

*Great Reviews* Hunter Mtn. Close/Cozy/Clean Condo

*Clean, cozy studio condo in the Village of Hunter featuring vintage decor. Short walk to the Ski Slopes, Snowtubing Park, Scenic Skyride, Dolan's Lake/Beach, Schoharie Creek, Fly Fishing, Hiking, Disc Golf, Stores, Eateries & Trailways Bus Stop. A Murphy bed w/ full size comfy Casper Mattress, a sectional couch, kitchen, microwave, electric wood stove, dinette, full bath, strong WiFi, Smart TV (no cable) w/Netflix, HBOGO, Pandora. No Pets/No Smoking or vaping in or on the property. Thanks

May 29 – Jun 5

G$15,629 GYD per night

Guest favorite

Condo in Saratoga Springs

4.98 out of 5 average rating, 135 reviews

Owl's Nest - Unique Condo in Vintage Location

This unique second floor condo is flooded with natural light. Steps from Congress Park and downtown Broadway, and a short walk to the Saratoga Race Course. Skylights, hardwood floors, keyless entry, custom lighting, complete kitchen with stainless steel appliances, air conditioning, small washer/dryer all housed in an original Skidmore College building creating a quiet space in a residential neighborhood. On-site parking is included. Intimacy surrounded by all the excitement of Saratoga.

Dec 25 – Jan 1

G$37,890 GYD per night

Guest favorite

Condo in Albany

4.89 out of 5 average rating, 162 reviews

Elegant, spacious studio apt in historic mansion

Welcome to the Plaza Suite, a newly renovated studio condo in an historic Center Square mansion. Enter through a grand reception hall/art gallery and climb the oak staircase to the sunny and spacious second floor apartment. There's a nice view of State Street and the Empire State Plaza. Features include: a new fully equipped kitchen, comfy lounge area, dining /work table, renovated vintage bathroom, walk-in closet and new queen bed. Feel free to enjoy a glass of wine in the art gallery.

Nov 28 – Dec 5

G$20,351 GYD per night

Guest favorite

Condo in Middletown

4.97 out of 5 average rating, 105 reviews

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kichen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking, swimming pool. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

Feb 21 – 28

G$25,062 GYD per night

Guest favorite

Condo in Lanesville

4.92 out of 5 average rating, 114 reviews

The Views! Beautiful Hunter Mtn. 1BR.

This is THE location on Hunter Mtn. Ski and hike the best trails from the backyard! Take in mountain views from deck. Decorated in modern ski decor that celebrates all 4 beautiful seasons. Maximize all of your mountain time, with this Liftside condo and enjoy apres ski & the many other area activities. Cable, wifi, gas fireplace. Work-space which includes a desk and monitor hook up. Clean linens/towels, coffee bar, laundry. Stocked kitchen & bath. Board games galore. Guide books.

Jun 12 – 19

G$29,696 GYD per night

Guest favorite

Condo in Brattleboro

4.92 out of 5 average rating, 286 reviews

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

Sep 19 – 26

G$18,962 GYD per night

Guest favorite

Condo in Hunter

4.98 out of 5 average rating, 538 reviews

Hunter Mtn Liftside Ski In/Out, Slopeside!

Fantastic location! Liftside! Beautifully renovated SLOPESIDE ski on/ski off condo . Spacious one bedroom condo with fully stocked kitchen, luxurious bathroom with jacuzzi tub, large bedroom with queen bed, and comfortable, cozy open concept living and dining room. Real wood burning fireplace. Private deck backs up to the ski slopes at Hunter Mountain! Seconds away from the Kaaterskill Flyer lift , main lodge, and bar. Avail for seasonal rental 11/15-4/15 $15000

Aug 5 – 12

G$22,660 GYD per night

Guest favorite

Condo in West Dover

4.94 out of 5 average rating, 181 reviews

Comfy Condo - 2 Min Walk to Carinthia Grommet Lift

One BR condo. Corner unit, 1st floor. 2 min walk to Carinthia Magic Carpet. Minutes drive to golf and mountain biking. 1 BR with Queen bed and full bath with jetted tub. Sofa bed and wood burning fireplace in LR. TV with DVD and Roku in LR. WiFi. Kitchen is small but has everything. Washer/dryer. Storage closet for skis & clubs. Plenty of dining nearby. Perfect for couples, solo adventurers, and small families. Plenty of parking on site.

Aug 4 – 11

G$22,347 GYD per night

Guest favorite

Condo in Saratoga Springs

4.98 out of 5 average rating, 214 reviews

Best Location Racing Season, Broadway, The Belmont

Weekly rentals for racing season, Monday-Monday. Stroll through Congress park past the Casino to Caffe Lena, Preservation Hall, Saratoga City Center, Broadway restaurants & shopping from our lovely first floor 1 Bdrm condo. 1 block to Congress Park. 3 blocks to the Track. Short drive to the Spa Little Theatre, Skidmore College, SPAC, The Baths, The Harness Track, The Dance Museum, The State Park and so much more!

Jun 6 – 13

G$178,847 GYD per night