Immerse yourself in the allure of Berkshires, a stunning spot in Massachusetts that’s known for its cottages. Choose from 1,550 diverse options to tailor your perfect trip.

Find your perfect cottages in Berkshires that fits both your style and budget. With prices ranging between $49 and $13,396, enjoy top-notch amenities like Internet / Wifi.

Top Features: Internet / Wifi, Kitchen / Kitchenette, Air conditioner, Parking and TV

Local Highlights: Bridge of Flowers, Stanley Park, Springfield Museums, Northwest Park and New England Air Museum

Take the first step towards an unforgettable Berkshires experience. Reserve your cottages today and uncover the hidden gems of Massachusetts.

Top Cottages in Berkshires

Property grounds
4.8
Outstanding(169 Reviews)
Cottage
 in Harwinton
Waterfront Lake Home on Tranquil Harwinton Lake with spectacular 180⁰ view.
4 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed

This Cottage for $348 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Exterior
4.8
Outstanding(176 Reviews)
Cottage
 in Salisbury
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Pets allowed

Discover the beauty of Berkshires with a stay at Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views, a top rated Cottage with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

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Fridge, microwave, oven, stovetop
5.0
Outstanding(95 Reviews)
Cottage
 in New Marlborough
Quiet rustic cottage with shared lake access
6 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner
Most favorited

Nestled in Berkshires, this Cottage is perfect for your next vacation. Enjoy Quiet rustic cottage with shared lake access's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.

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Property grounds
4.9
Outstanding(97 Reviews)
Cottage
 in Lanesboro
Charming historic cottage on scenic road to Mt. Greylock
5 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Berkshires, at $227 per night for your next great vacation.

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Property view
4.8
Outstanding(86 Reviews)
Cottage
 in Warren
Beautiful Cottage and Waterfront Access
4 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Experience vacation in Berkshires with our Cottage, Beautiful Cottage and Waterfront Access. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Exterior
4.9
Outstanding(78 Reviews)
Cottage
 in Bethlehem
Quaint cottage located directly on Long Meadow Pond
6 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Quaint cottage located directly on Long Meadow Pond, our elegant Cottage in Berkshires. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more.

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Exterior
4.8
Outstanding(69 Reviews)
Cottage
 in Lakeville
Summer Lake Cottage, private beach, Berkshire Hills, small village
18 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our Cottage in Berkshires has everything you need for a rejuvenating stay. Treat yourself to Summer Lake Cottage, private beach, Berkshire Hills, small village's exceptional amenities, such as Dishwasher, Fireplace and Internet / Wifi.

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View from property
5.0
Outstanding(55 Reviews)
Cottage
 in Lenox
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
5 guests · 2 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

Indulge in a peaceful retreat at Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA, our elegant Cottage in Berkshires. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.

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Fridge, microwave, oven, stovetop
5.0
Outstanding(53 Reviews)
Cottage
 in New Marlborough
Charming Cottage, New Marlborough Village Green in the Berkshires
4 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Berkshires, at $254 per night for your next great vacation.

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On the beach, sun loungers
5.0
Outstanding(54 Reviews)
Cottage
 in New Preston
Lovely Cottage, Completely Remodeled Two Bedroom One Bath Can Accommodate Six.
6 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

This inviting Cottage in Berkshires can fit your needs for many types of vacations, at $388 per night.

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Outdoor dining
4.8
Outstanding(60 Reviews)
Cottage
 in Monterey
\nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires
5 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Berkshires? Look no further than our Cottage, \nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Property grounds
5.0
Outstanding(50 Reviews)
Cottage
 in Otis
Woodland Cottage (EST. 2020) Convenient, private, family friendly
8 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our Cottage in Berkshires has everything you need for a rejuvenating stay. Treat yourself to Woodland Cottage (EST. 2020) Convenient, private, family friendly's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.

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Vacation rentals with internet & wifi in Berkshires

Beach
4.7
Outstanding(62 Reviews)
Cottage
 in Bethlehem
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
6 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Looking for the perfect place to call home during your trip to Berkshires? This Cottage offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace and Internet / Wifi, and more.

$$$$
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Lake
4.7
Outstanding(64 Reviews)
Cottage
 in Tolland
Relax And Enjoy A Fun Getaway At The Bacchus Cottage!
5 guests · 2 bedrooms · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

This Cottage for $169 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property grounds
4.8
Outstanding(51 Reviews)
Cottage
 in New Marlborough
Perfect Vacation Get Away - Historical New Marlborough
4 guests · 1 bedroom · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Berkshires at Perfect Vacation Get Away - Historical New Marlborough for $272 for your next trip.

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Exterior
5.0
Outstanding(43 Reviews)
Cottage
 in Great Barrington
Romantic Berkshires Cottage - Stunning Views, Pool
3 guests · 1 bedroom · 1 bath
Garden · Pool · Pets allowed

Business stays, family stays, couples stay, getaway vacation, and rental in Berkshires at Romantic Berkshires Cottage - Stunning Views, Pool for $279 for your next trip.

$$$$
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Exterior
5.0
Outstanding(43 Reviews)
Cottage
 in Becket
Lakefront Cottage In The Berkshires In Western Massachusetts
4 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Internet / Wifi · Parking

Indulge in a peaceful retreat at Lakefront Cottage In The Berkshires In Western Massachusetts, our elegant Cottage in Berkshires. Enjoy amenities including Internet / Wifi, Balcony / Patio and Kitchen / Kitchenette, and more.

$$$$
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Interior
4.9
Outstanding(45 Reviews)
Cottage
 in Great Barrington
Berkshire Mountain Cottage: in the Heart of the Berkshires
4 guests · 2 bedrooms · 1 bath
Garden · Pets allowed · Kitchen / Kitchenette

Experience vacation in Berkshires with our Cottage, Berkshire Mountain Cottage: in the Heart of the Berkshires. Enjoy amenities such as Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Exterior
5.0
Outstanding(40 Reviews)
Cottage
 in Winchester
Our Cottage - Small in size, Big in character, On beautiful Highland Lake
6 guests · 2 bedrooms · 1 bath
Garden · Pool · Kitchen / Kitchenette

This Cottage for $304 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Exterior
4.8
Outstanding(43 Reviews)
Cottage
 in Otis
Charming cedar shingle cottage
7 guests · 3 bedrooms · 1 bath
Kitchen / Kitchenette · Internet / Wifi · Parking

Discover the beauty of Berkshires with a stay at Charming cedar shingle cottage, a top rated Cottage with amenities such as Dishwasher, Fireplace and Internet / Wifi, and more.

$$$$
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Property grounds
5.0
Outstanding(30 Reviews)
Cottage
 in Tyringham
Ashintully Cottage in spectacular setting
6 guests · 4 bedrooms · 3 baths
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Experience vacation in Berkshires with our Cottage, Ashintully Cottage in spectacular setting. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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Fridge, microwave, oven, stovetop
4.8
Outstanding(32 Reviews)
Cottage
 in Hillsdale
Beautiful, Unique Country House w/Large Deck
2 guests · 1 bedroom · 1 bath
Garden · Kitchen / Kitchenette · Air conditioner

The best choice in Berkshires for Cottage, for $208 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property grounds
4.9
Outstanding(28 Reviews)
Cottage
 in Stockbridge
Rustic Waterfront Retreat With Private Dock, 2 kayaks & canoe. Air conditioner!
6 guests · 2 bedrooms · 1 bath
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

This Cottage for $247 in Berkshires, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Terrace/patio
5.0
Outstanding(27 Reviews)
Cottage
 in Morris
Bantam Lake Cottage - Lake access, 6 kayaks, 2 SUP, fire pit, grill and games.
6 guests · 2 bedrooms · 2 baths
Garden · Pets allowed · Kitchen / Kitchenette

This inviting Cottage in Berkshires can fit your needs for many types of vacations, at $419 per night.

$$$$
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