Apartment vacation rentals in Pittsfield

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Top-rated apartment rentals in Pittsfield

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Guest favorite

Apartment in Shelburne Falls

4.98 out of 5 average rating, 488 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a newly renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Feb 14 – 21

G$29,119 GYD per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 260 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 11 – 18

G$21,142 GYD per night

Guest favorite

Apartment in Greenfield

4.96 out of 5 average rating, 270 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen bed & desk. Apt. Is 2 min's to Rt. 2 Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes.

Jul 3 – 10

G$23,273 GYD per night

Superhost

Apartment in Lee

4.79 out of 5 average rating, 107 reviews

Cozy Berkshire Cottage Style Apartment

Stay in a cozy Berkshires apartment! All windows allow views to the peaceful surrounding state forest and yard. Watch humming birds, oriols, deer, squirrels, opossums, racoons, woodchucks, and many more... The house is set back from the road, easily accessible, yet private. The cottage is a duplex: the Airbnb apartment is on the left side of the cottage. • Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Stockbridge, Lenox, MA Turnpike • Ideal for lovers of nature & the Berkshires

Apr 17 – 24

G$23,694 GYD per night

Guest favorite

Apartment in Plainfield

4.97 out of 5 average rating, 238 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Mar 11 – 18

G$24,875 GYD per night

Guest favorite

Apartment in Northampton

4.98 out of 5 average rating, 650 reviews

Tree Top Suite, cozy downtown apartment

This is an entire apartment, close to downtown. It is on the third floor, so you will have to walk up two flights of stairs. Because there are dormers (peaked areas in the ceiling), especially tall people might feel a little cramped in this space. There is a king size bed in the bedroom, a living area that includes a kitchenette, dining area, seating area and a smart TV with a fire stick, and a large bathroom. Outdoor seating on the front porch is for your use only.

Mar 8 – 15

G$21,829 GYD per night

Guest favorite

Apartment in Northampton

4.95 out of 5 average rating, 280 reviews

Bike Path Hideaway Near Smith, Cooley, Northampton

Modern cozy 1BR with living space, private bathroom, private driveway, screened porch, coded door, and inflatable hot tub! Wooded neighborhood. Bike path along river. 5 min. drive to Look Park. 10 min. drive to Northampton. BR has luxury queen bed, single bed, AC. Cozy LR, WiFi, 55" TV, equipped kitchen. Near excellent hikes. A family lives in attached unit so there is some noise, not during sleep hours. Cats have lived here in the past. Great getaway spot!

Sep 18 – 25

G$21,373 GYD per night

Guest favorite

Apartment in North Adams

4.96 out of 5 average rating, 422 reviews

Steps to MoCA, 2bd + SAUNA!

This 2 bedroom apartment occupies the parlor floor of the Small Mansion of Chase Hill, located within 3 minutes walking distance to Mass MoCA. 5 mins walk to downtown’s restaurants. 5-10 mins drive to Williams, MCLA, Clark. Whimsically restored (yes, fast Wi-Fi & great water pressure). YOUR STAY ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO! Our 2 other listings on airbnb.com: /h/2chasehill and /h/chasehill2

Nov 24 – Dec 1

G$35,540 GYD per night

Superhost

Apartment in Adams

4.85 out of 5 average rating, 123 reviews

full apartment in adams and self check in

nice apartment on first floor in adams mass near mt greylock(URL HIDDEN) also 2 miles to greylock glen at the base of the mountain for hiking & biking trails 5 miles from mass moca 5 miles from mcla 12 miles from clart art & williams college 10 miles mt greclock peak 18 miles from jiminy peak , a ten mlle bike trail about 1000 feet from house also 23 miles & 40 minutes to tanglewood

Jul 15 – 22

G$22,538 GYD per night

Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 170 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Jun 14 – 21

G$15,311 GYD per night

Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 225 reviews

Marie's Place

This newly renovated bright sunny apartment is minutes from Bosquet ski area & also close to downtown. It has a large kitchen and pantry. Beautiful oak dining room table. Comfy living room set, with a 43 inch Roku TV. Electric fireplace. Queen size beds in both bedrooms. Large walk-in closet in. 28 minutes from Jiminy peak. Close to downtown restaurants and theaters.

Apr 11 – 18

G$30,721 GYD per night

Guest favorite

Apartment in Plainfield

4.95 out of 5 average rating, 237 reviews

Sunny carriage house apartment

Our sunny apartment is located midway between Northampton and the Berkshires, in a lovely rural setting. The kitchen, bath and studio living area are in a private apartment, surrounded by 12 acres of open fields. The kitchen is well equipped and includes all the makings for tea and coffee. Orange juice, oatmeal, English muffins and homemade granola are also provided!

Aug 12 – 19

G$24,660 GYD per night