Pet-friendly holiday rentals in Williamstown

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Top-rated pet-friendly home rentals in Williamstown

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Guest favourite

Guesthouse in North Adams

5.0 out of 5 average rating, 208 reviews

Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

23–30 Nov

$414 NZD per night

Guest favourite

Apartment in North Adams

4.91 out of 5 average rating, 394 reviews

Private guest apartment. One block from downtown.

Private guest apartment located on quiet dead end street on 1 acre of tree lined land. Super spacious and full of character , this first floor apartment is centrally located between MassMoCA and MCLA, and only one block from downtown North Adams . The main bedroom has a queen sized bed. The spare room, off of the living room , is smaller but has enough space for a comfy full size bed, and a closet . The pullout sofa in the living room also sleeps 2. A perfect spot for your Berkshire getaway!

19–26 Jun

$385 NZD per night

Superhost

Apartment in Williamstown

4.86 out of 5 average rating, 198 reviews

Williamstown Apt. on Green River Walk to Williams!

This Charming 3 bedroom apartment has hosted celebrities, published authors and world travelers. A deep sleep is guaranteed as the sounds of the Green River lull you to bed. You face the Green River when you sit on the back deck. Convenient to hikes across the street at the the Taconic Golf course, Williams College just two blocks away, The Clark Art is a 15 minute walk, and the apartment is perfect when you want to walk and explore the restaurants that offer take out in Williamstown, MA.

26 Aug – 2 Sep

$387 NZD per night

Guest favourite

Cottage in Williamstown

4.9 out of 5 average rating, 165 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 full futon. Dog friendly for up to 2 dogs .More than two dogs will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

25 Jul – 1 Aug

$361 NZD per night

Superhost

Home in Pownal

4.91 out of 5 average rating, 100 reviews

Quiet Vermont Home with Amazing View

Beautiful, quiet location just over the border of Vermont. It is located 5 minutes from Williams College, 15 Minutes from Mass MOCA, 15 minutes from Bennington. 30 minutes from Jiminy Peak, 1 hour from Stratton & Mount Snow. The house is perfect for a family and offers a beautiful master bedroom with master bathroom. The full wrap around porch will be equipped with an outdoor table and chairs in the warmer months. A beautiful setting to get away but an easy drive to neighboring towns.

22–29 May

$429 NZD per night

Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 264 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

20–27 Apr

$280 NZD per night

Superhost

Cottage in Florida

4.82 out of 5 average rating, 102 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

ENJOY A MOUNTAIN ADVENTURE You will fall in love with this magic cottage nestled within 2 acres of old growth forest. Breathe in the fresh air enjoying the mountain vistas and sipping some hot cocoa. Warm up by the pellet stove or gaze at the stars seating by the fire pit. Berkshire East Ski is a few min away as well as the famous hairpin turn and many national forests. MASS MoCA only 15 min away, and Mt. Greylock is nearby as well as many outdoor adventures, restaurants & pubs.

6–13 Dec

$296 NZD per night

Guest favourite

Guest suite in Charlemont

4.9 out of 5 average rating, 182 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

7–14 Mar

$248 NZD per night

Guest favourite

Bungalow in Williamstown

4.89 out of 5 average rating, 202 reviews

Hollywood Bungalow in the Berkshires

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

24 Nov – 1 Dec

$466 NZD per night

Guest favourite

Farm stay in New Ashford

4.9 out of 5 average rating, 221 reviews

Sheep Barn on the Greylock Valley Estate

Located 10 minutes from Williamstown, the Sheep Barn is a completely renovated antique barn, with 3 bedrooms, 2 full baths, and full kitchen. It's the perfect place for spring and summer getaways, cozy fall weekends, and winter ski vacations. Offering hiking trails and complete privacy, it is still close to Williams College, Jiminy Peak, and other Northern Berkshire attractions. During winter months we recommend that guests have All Wheel Drive vehicles.

24 Feb – 3 Mar

$341 NZD per night

Guest favourite

Guesthouse in Lenox

4.95 out of 5 average rating, 284 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.

6–13 Sep

$276 NZD per night

Guest favourite

Loft in East Nassau

4.99 out of 5 average rating, 154 reviews

Dog Friendly Farm Spring bird watching

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

13–20 Sep

$294 NZD per night