Vacation rentals in New Ashford

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Top-rated vacation rentals in New Ashford

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Top guest favorite

A red carriage house is set against a backdrop of mountains and blue skies. White Adirondack chairs circle a stone fire pit, while a picnic table and umbrella provide additional outdoor seating. Lush greenery surrounds the area, creating a serene environment.

Guesthouse in North Adams

5 out of 5 average rating, 271 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.

Guest favorite

A charming stone building is surrounded by lush greenery and colorful flowers, including pink and white blossoms. The sign, featuring 'Stone School Cottage,' is prominently displayed. Large windows indicate a bright interior. The setting offers a peaceful and inviting entrance to the accommodation.

Cottage in Lanesborough

4.93 out of 5 average rating, 244 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Top guest favorite

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 185 reviews

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Guest favorite

A gentle stream flows through a wooded area, surrounded by trees with bare trunks and patches of moss-covered rocks. Fallen leaves cover the ground, and the sound of flowing water is evident in this serene natural setting.

Cottage in Williamstown

4.89 out of 5 average rating, 188 reviews

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog 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!

Top guest favorite

An open door reveals the entryway of a rustic cabin. A patterned rug leads into a softly lit interior, where a cozy bed is visible in the background, framed by natural wood accents and windows that invite the outside in.

Cabin in Cummington

4.98 out of 5 average rating, 213 reviews

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Guest favorite

A panoramic view of a snow-covered mountain, featuring illuminated ski runs that carve down the slopes. The surrounding trees are blanketed in snow, while a cozy cluster of buildings can be seen at the mountain's base, glimmering softly in the evening light.

Apartment in Lanesborough

4.89 out of 5 average rating, 127 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm

Guest favorite

A countertop is seen with a Keurig coffee maker, a wine rack holding varying colored glasses, and a framed botanical print. A small potted plant adds a touch of greenery, creating a welcoming area for refreshments.

Apartment in Williamstown

4.94 out of 5 average rating, 101 reviews

Williamstown apt close to Williams College & MoCA.

Second floor 1 bedroom (Queen) and 1 bathroom apartment with private entrance. This cozy Williamstown retreat will provide exactly what you would expect in the Berkshires. Walking distance to downtown Williamstown and the newly created bike path. This unit provides off street parking with plenty of privacy, and can truly transform your stay. Less than 5 Miles to MASS MoCA. 25 Minutes to Jiminy Peak. 1.5 Miles exactly to the center of Spring St. .4 Miles to the bike path entrance.

Guest favorite

A quaint cottage is nestled among trees, featuring a welcoming front porch with several potted plants and outdoor seating. The light-colored exterior is complemented by blue accents on the chairs, while the wooden deck extends invitingly, creating a serene outdoor space.

Cabin in Cheshire

4.89 out of 5 average rating, 164 reviews

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

Guest favorite

A wooden sign displays the name 'Ashuwillticook Rail Trail' against a backdrop of lush greenery and a serene water view. The sign features clear lettering, and nearby information boards are visible, providing details for visitors. The scene conveys a peaceful outdoor setting.

Guest suite in Adams

4.85 out of 5 average rating, 101 reviews

Quaint Suite in Center of Adams

Pet Friendly mother-in law suite within a beautiful Victorian home in the center of Adams. The quaint town sits at the base of Mount Greylock with hiking and bike trails within minutes of your accommodations. Restaurants, grocery store and a 9 hole golf course are in walking distance. MASS MOCA is just a short 6 mile drive. Tanglewood music center is a 35 minute drive. Beautiful deck with gas firepit and grill. We would love you to be our guest.

Top guest favorite

An inviting wood-fired Finnish sauna is presented with a circular wooden interior. A small stove, burning warmly, is visible along with benches along the walls. Natural light filters in through a glass door, creating a soothing atmosphere.

Home in North Adams

4.98 out of 5 average rating, 425 reviews

Steps to MoCA private house + SAUNA!

Tucked away on a hilltop oasis above MoCA (3 minutes by walk) the whimsically restored house is part of a private estate. 10 min drive to Williams College & Clark. Steps to downtown & restaurants. Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

Superhost

A flowing stream is nestled among lush greenery, bordered by tall trees and dense foliage. Clear water glistens as it travels over smooth stones, with soft ripples audible in the serene environment.

Yurt in Stephentown

4.9 out of 5 average rating, 126 reviews

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!

Superhost

An ironing board is positioned against a wall, featuring a patterned cover. A turquoise laundry basket stands nearby, while a small window allows natural light into the space. The floor showcases a decorative tile design, adding visual interest to the room.

Apartment in Adams

4.85 out of 5 average rating, 135 reviews

full apartment in adams 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

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Popular amenities for New Ashford vacation rentals

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Other great vacation rentals in New Ashford

An outdoor deck is presented with a large wooden table surrounded by chairs. Colorful cushions add comfort, and potted flowers brighten the space. Soft string lights hang above, illuminating a hammock and lounge chairs nearby, all set against a backdrop of lush greenery.

Guest suite in Hancock

4.81 out of 5 average rating, 180 reviews

Cozy apartment near Jiminy Peak

KatieRating, 5 stars3 months ago

We loved staying with Naren! She was very accommodating and has a beautiful home:) Highly recommend and would love to return!

Guest favorite

An outdoor bar setup is presented, featuring a rustic wooden bar adorned with various bottles and glasses. Two wooden barrels stand on either side of the bar, all surrounded by lush greenery, enhancing the natural setting and inviting gathering.

Home in New Ashford

4.91 out of 5 average rating, 199 reviews

Rosecroft, Historic Home, Greylock Valley Estate

AntoninoRating, 5 stars2 weeks ago

Awesome location and great house in general!

Guest favorite

An aerial view captures the expansive Jiminy Peak Resort, showcasing a snow-covered landscape dotted with trees and ski slopes in the background. The modern condominium complex sits prominently in the foreground, with parking spaces visible in front and mountain trails leading into the distance.

Home in Hancock

4.94 out of 5 average rating, 32 reviews

Bougie B’s Mountainside Getaway

TheresaRating, 5 stars3 months ago

Absolutely beautiful space. Spotlessly clean. Full kitchen amenities plus a little coffee station. Fabulously comfortable beds and living room furniture. Deliciously soft towels. Just an overall great experience and peaceful stay!!

Guest favorite

A two-story house is framed by sunflowers in the foreground, with a porch extending across the front. The roof features gables and multiple windows, allowing for ample natural light. The backdrop displays soft, colorful clouds in the sky, enhancing the serene landscape.

Home in Adams

4.92 out of 5 average rating, 59 reviews

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

StewRating, 5 stars1 week ago

We had two large dinners at Jay's house and it was perfect for hosting 22 people. THe beds were comfortable, there were all the knives and kitchen gadgets we needed to serve dinner to 22 people two nights in a row. The property is beautiful: lush and green.

Farm stay in Adams

5 out of 5 average rating, 3 reviews

Berkshires/Pet Friendly farm stay w/mountain views

IsabelleRating, 5 stars2 weeks ago

My three friends and I had a wonderful weekend stay at this airbnb. From the start Jessica, the host, was in touch and responsive to any questions I had. The RV itself was perfect, exactly what my group was looking for and was as advertised. A lovely guest-ready camper, a fire pit, great views and outdoor spaces, accessibility, chairs with an umbrella, a picnic table, a hammock that could be set up, easy storage for all of these things, and friendliness from the host next door. We were able to comfortably sleep 4 people for 3 nights. My group have discussed returning when we can because we had such a positive experience. We hope that others will get the opportunity to make memories in Adams, MA as we did during our stay this summer. All I have to say are good things about this location and the people who run it. I would absolutely recommend it :)

Top guest favorite

Cabin in East Nassau

5 out of 5 average rating, 46 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

ChristineRating, 5 stars3 days ago

The space is luxurious and stunning even more beautiful than the photos, so thoughtfully designed and really helped us feel at home at once. Matt and Sarah were so helpful whenever we had any questions. We had such a relaxing stay and feel so grateful to have been able to enjoy the space!

Top guest favorite

A set of double doors features rustic wood with an X-pattern design, providing an inviting entryway. The doors are fitted with black handles and surrounded by a white trim, complementing the warm wooden flooring visible in the foreground.

Apartment in Adams

4.99 out of 5 average rating, 74 reviews

Charming/Rustic Apartment with downtown views

JeffRating, 5 stars1 week ago

Adams is a beautiful little town, and Michele's place is right in the middle of it. Everything was as described and was VERY clean and comfortable. I was there for the MoCA in North Adams, access to Mount Greylock, and the rail trail and this was the perfect location. The weather thwarted many of my plans, but this place was plenty cozy enough to just hang out in and wait for breaks in the rain! I would definitely stay here again! Michele is a wonderful host, friendly and responsive.

The Victorian farmhouse features intricate architectural details on the porch, including decorative trim. Greenery surrounds the entrance, with a large garden and trees visible in the background. A pathway leads from the porch to the adjacent yard, enhancing the home's inviting appearance.

Home in Adams

4.93 out of 5 average rating, 247 reviews

1890 House

Wen OngRating, 5 stars3 weeks ago

kate’s home was a cozy and peaceful retreat. she was super responsive, even with our late check-in, and the house had everything we needed to unwind — especially the fireplace, which we used almost every day. the kitchen was well-equipped, and we loved exploring the local food spots and hiking trails nearby. overall, a lovely stay — we’d definitely come back!

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Vacation rentals in New Ashford

Top-rated vacation rentals in New Ashford

Vacation rentals for every style

Popular amenities for New Ashford vacation rentals

Other great vacation rentals in New Ashford

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