Apartment holiday rentals in Pittsfield

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Top-rated apartment rentals in Pittsfield

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Guest favourite

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!

30 Mar – 6 Apr

$192 NZD per night

Guest favourite

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!

7–14 Oct

$211 NZD per night

Guest favourite

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.

3–10 Jul

$211 NZD 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

17–24 Apr

$233 NZD per night

Guest favourite

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!

10–17 Mar

$232 NZD per night

Guest favourite

Apartment in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

22–29 Aug

$243 NZD per night

Guest favourite

Apartment in North Adams

4.97 out of 5 average rating, 411 reviews

See MoCA from your mansion+Sauna!

Situated on a hilltop oasis right above Mass MoCA, this apartment occupies the second and third floor of the Small Mansion of Chase Hill, a private historic estate in the heart of North Adams. 3 minutes walk to MoCA. Steps to downtown’s restaurants. 5-10 mins drive to Williams, MCLA, Clark. Whimsically restored (yes, fast Wi-Fi & great water pressure). Home to the Floating Tower Artist Retreat. YOUR STAY ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

14–21 Dec

$310 NZD per night

Superhost

Apartment in New Lebanon

4.95 out of 5 average rating, 128 reviews

Sunny Duplex at the old boarding house

Charming big vintage apartment for up to a family of five in an old boarding house from 1900. It's a Greek Revival house on a country lane at the foot of the Berkshires. Master bedroom and full bath are downstairs, where there is also a lovely living room, fully stocked kitchen and mudroom with washer/dryer. 2nd bedroom and side room in the attic upstairs. Small front sitting porch, big side lawn and flowery backyard with grill and table.

3–10 Oct

$249 NZD 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

15–22 Jul

$204 NZD per night

Guest favourite

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.

14–21 Jun

$145 NZD per night

Guest favourite

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.

11–18 Apr

$305 NZD per night

Guest favourite

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!

12–19 Aug

$227 NZD per night