Vacation rentals in Lanesborough

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Top-rated vacation rentals in Lanesborough

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Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 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.

Oct 4 – 11

R3,495 ZAR per night

Guest favorite

Apartment in Lanesborough

5.0 out of 5 average rating, 21 reviews

Cozy Berkshire Waterfront Home

Welcome to our charming waterfront home on Pontoosuc Lake! The Berkshire Lakescape is perfect for a romantic getaway for a couple or two, or a solo adventure away. Soak in lake views from the deck or try to catch a stunning sunset from the water’s edge. Kayak straight from our backyard and return for marshmallows at the firepit. Explore Berkshires' culture and outdoor activities - Tanglewood, Mount Greylock, and more are just a short drive away. We can't wait to host you for a memorable stay.

Jun 11 – 18

R3,805 ZAR 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.

Nov 24 – Dec 1

R3,066 ZAR per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

Oct 23 – 30

R2,292 ZAR per night

Guest favorite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

Nov 26 – Dec 3

R1,817 ZAR per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Aug 19 – 26

R1,672 ZAR per night

Superhost

Apartment in Lanesborough

4.85 out of 5 average rating, 62 reviews

Charming Apt. in 18th c. Berkshire Farmhouse

This lovely 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 cute apartments. 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. *Check out our other rentals on our profile!* Follow us on IG @SecondDropFarm

Sep 10 – 17

R2,041 ZAR per night

Superhost

Cabin in Lanesborough

4.83 out of 5 average rating, 53 reviews

Cozy stream-side cabin

Nestled in the heart of the Berkshires along a cool, fresh-water stream. This 1-bedroom 650 sq. ft. bungalow has been completely renovated and ready to welcome you. It is conveniently located to many area attractions and is situated near the base of Mount Greylock, the highest peak in Massachusetts. The main living space has a working brick fireplace, cathedral ceilings, recessed lighting, a French door, real pine wood walls, and a loft that overlooks the main living space.

Oct 4 – 11

R2,911 ZAR per night

Guest favorite

Cabin in Cheshire

4.89 out of 5 average rating, 152 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.

Jun 12 – 19

R2,707 ZAR per night

Guest favorite

Apartment in Pittsfield

4.92 out of 5 average rating, 25 reviews

Comfortable Pittsfield Loft

Located in the center of the Berkshires, this newly renovated Pittsfield apartment is comfortable and convenient. Come enjoy the new kitchen and delightful walk in shower. Centrally located to all of the wonderful Berkshires attractions this one bedroom apartment offers new appliances, driveway parking, washer and dryer. Yuhong and Mike live on-site in the apartment below and they are dedicated to providing an excellent guest experience. THIS IS A NO SMOKING APARTMENT

Nov 6 – 13

R1,426 ZAR per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Jul 18 – 25

R2,889 ZAR per night

Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 249 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016), private cottage set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. For conditions message Jill.

Oct 25 – Nov 1

R5,415 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Lanesborough vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Lanesborough's top sights

Jiminy Peak200 locals recommend

Mount Greylock State Reservation Visitor Center39 locals recommend

Olde Forge Restaurant39 locals recommend

Bob's Country Kitchen6 locals recommend

Ashuwillticook Rail Trail74 locals recommend

Whitney's Farm Market & Garden Center20 locals recommend

Other great vacation rentals in Lanesborough

Guest favorite

Apartment in Pittsfield

4.96 out of 5 average rating, 48 reviews

The sweet place in the beautiful Berkshires!

Nov 28 – Dec 5

R2,376 ZAR per night

Guest favorite

Home in Lanesborough

5.0 out of 5 average rating, 47 reviews

Scenic mountain getaway.

Oct 31 – Nov 7

R5,315 ZAR per night

Guest favorite

Home in Lanesborough

5.0 out of 5 average rating, 88 reviews

Tranquil mid-century modern Berkshires retreat

Dec 18 – 25

R7,153 ZAR per night

Guest favorite

Home in Lanesborough

4.93 out of 5 average rating, 15 reviews

The Pond House

Nov 21 – 28

R4,684 ZAR per night

Guest favorite

Cottage in Lanesborough

4.98 out of 5 average rating, 46 reviews

Amazing 2 bedroom lake front cottage, large patio

Dec 25 – Jan 1

R7,747 ZAR per night

Guest favorite

Home in Lanesborough

4.95 out of 5 average rating, 19 reviews

Chic Berkshire Retreat by Evergreen Home

Oct 4 – 11

R4,940 ZAR per night

Guest favorite

Home in Lanesborough

4.98 out of 5 average rating, 55 reviews

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Aug 27 – Sep 3

R5,244 ZAR per night

Guest favorite

Home in Lanesborough

4.95 out of 5 average rating, 88 reviews

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

Dec 10 – 17

R16,385 ZAR per night

Show all

Quick stats about vacation rentals in Lanesborough

Total rentals
180 properties
Rentals with a pool
120 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
110 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
R1,140 ZAR before taxes and fees

Frequently Asked Questions

What are the most popular amenities for Hotel Rentals in Lanesborough?
Enhance your stay in our Hotel Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Lanesborough vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 120 vacation homes with pools in Lanesborough, available on Airbnb. Make a splash and soak up the sun in style!
Do apartment rentals in Lanesborough have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Lanesborough. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Lanesborough have free parking?
Absolutely! We offer over 20 condo rentals with free parking in Lanesborough. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Lanesborough?
Yes! Work meets play with ease at over 60 vacation rentals in Lanesborough featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Lanesborough?
Experience the best of Lanesborough with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Lanesborough?
Four-legged friends are welcome in Lanesborough. Choose from more than 30 vacation rentals for guests traveling with pets.
Do apartment rentals in Lanesborough have air conditioning?
Absolutely! We offer over 20 apartment rentals with air conditioning in Lanesborough. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Lanesborough have wifi?
Absolutely! We offer over 50 house rentals with wifi in Lanesborough. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Lanesborough?
Lanesborough has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Lanesborough

Top-rated vacation rentals in Lanesborough

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Lanesborough vacation rentals

Stay near Lanesborough's top sights

Other great vacation rentals in Lanesborough

Apartment in Pittsfield

Home in Lanesborough

Home in Lanesborough

Home in Lanesborough

Cottage in Lanesborough

Home in Lanesborough

Home in Lanesborough

Home in Lanesborough

Quick stats about vacation rentals in Lanesborough

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What are the most popular amenities for Hotel Rentals in Lanesborough?

Are there Lanesborough vacation rentals on Airbnb with pools?

Do apartment rentals in Lanesborough have a kitchen?

Do condo rentals in Lanesborough have free parking?

Are there vacation rentals with a dedicated workspace in Lanesborough?

How much does it cost to stay in house rentals in Lanesborough?

Are there pet-friendly vacation rentals in Lanesborough?

Do apartment rentals in Lanesborough have air conditioning?

Do house rentals in Lanesborough have wifi?

Are there family-friendly vacation rentals in Lanesborough?

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