Stockbridge holiday homes

We found 773 holiday rentals — enter your dates for availability
Discover a selection of 35 homes and other holiday rentals in Stockbridge that are perfect for your trip. Whether you're staying in a holiday rental with your children and pets or just with friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Stockbridge

Showing deals for:11 Dec - 18 Dec

Exterior
Terrace/patio
Dining
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
NZ$4,194
for 7 nights, 1 cottage
NZ$599 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Cottage Entrance
Kitchen
2nd bedroom
Kitchen open to living room
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

Great Barrington

8% off
NZ$2,755
for 7 nights, 1 cottage
NZ$394 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Workstation with a view!
view from the 2nd bedroom
View from the lawn by the water
Open plan dining area with water views and access to the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,435
for 7 nights, 1 home
NZ$1,205 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Open kitchen to great room, wonderful for cooking and entertaining
The great room with wonderful water views and working fireplace
Sunroom has Queen pull out sofa bed
Hot tub overlooking the lake
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
NZ$7,994
for 7 nights, 1 home
NZ$1,142 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
House 1- Mountain views from this open concept kitchen, dining, sitting room
Property grounds
3 season Sunroom
Dining area and small sitting are with flat screen TV. Stairs to second floor
Exceptional
(6 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

11% off
NZ$10,497
for 7 nights, 1 home
NZ$1,500 per night
includes taxes & fees
Grand Estate w/ Mountain Views by Evergreen Home
Exterior
Private kitchen
Property grounds
Living area
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$6,440
for 7 nights, 1 home
NZ$920 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Enclosed porch- view into back yard- dining/game table
Kitchen with counter seating for 4- door on the right to garage
Outdoor dining
View from entry into living room- perfect spot for relaxing!
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
NZ$6,570
for 7 nights, 1 home
NZ$939 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Games room
Terrace/patio
Private kitchen
Property grounds
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

7% off
NZ$9,855
for 7 nights, 1 home
NZ$1,408 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Interior
Living area
Exterior detail
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,280
for 7 nights, 1 home
NZ$1,040 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Island with Kitchen drawer microwave, quartz countertops, refrigerator
Front showing deck on the side of the house in both levels
Looking towards outside deck and tiv area in fireplace sitting area
Interior
Exceptional
(133 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
NZ$4,165
for 7 nights, 1 home
NZ$595 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Reading nook with natural lighting
Fully screened porch!
Kitchen with stainless steel appliances
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

11% off
NZ$5,304
for 7 nights, 1 home
NZ$758 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Dining
Interior
Living area
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,716
for 7 nights, 1 cabin
NZ$674 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Staircase
You will love dining and working in this rich and colorful room
A mudroom off the back leads to the large wooden deck
Outdoor dining and grill on the 16' x 20' wooden deck.
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
NZ$6,052
for 7 nights, 1 home
NZ$865 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Living area
Private kitchen
Exterior
Living area
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Southfield

8% off
NZ$11,253
for 7 nights, 1 home
NZ$1,608 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Come and unwind.
Porch opens up from dining room. Ceiling fan and lights above.
Entrance view.
View of the river.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

Great Barrington

8% off
NZ$3,479
for 7 nights, 1 home
NZ$497 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Back patio with Hot Tub
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
NZ$9,584
for 7 nights, 1 home
NZ$1,369 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Second story deck with lake views, dining table for 8, sitting area and grill
Open kitchen area with bar seating, great for socializing while you meal prep.
Open and bright main floor living space with stunning views of Laurel Lake.
Living room with fireplace and forest views
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
NZ$6,734
for 7 nights, 1 home
NZ$962 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Room
Outdoor dining
Dining
Private kitchen
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
NZ$4,879
for 7 nights, 1 home
NZ$697 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Screened in porch
Terrace/patio
Queen bedroom
Property grounds
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,819
for 7 nights, 1 home
NZ$688 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Interior
Interior
Living area
Pool
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

7% off
NZ$5,496
for 7 nights, 1 home
NZ$785 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
dining area
River view from window
Blue House side entry from driveway
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
NZ$4,322
for 7 nights, 1 home
NZ$617 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Living Room
Great Barrington Castle house
Front view of home
Great Barrington Castle
Exceptional
(51 reviews)

NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE

Great Barrington

8% off
NZ$6,127
for 7 nights, 1 home
NZ$875 per night
includes taxes & fees
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Enjoy a beautiful crisp night under the lights
After a hard day on the trails or a long day on the town, relax in this oasis
Seamless entertaining with the wide open concept, living room -kitchen- patio
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
NZ$7,002
for 7 nights, 1 home
NZ$1,000 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,692
for 7 nights, 1 home
NZ$956 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The historical city of Stockbridge awaits you

Enjoy the area's museums, history and architecture with a rental holiday home in Stockbridge. Revered for its gardens, camping and hiking, this city is both romantic and relaxing. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Stockbridge

Are you looking for attractions to visit in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Stockbridge has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Wyndhurst Golf & Club (4.7 mi / 7.6 km)
  • Ski Butternut (7.2 mi / 11.6 km)
  • Bousquet Ski Area (9.1 mi / 14.6 km)
  • Catamount Ski Area (11.6 mi / 18.7 km)
  • Otis Ridge (12.9 mi / 20.8 km)
  • Jiminy Peak Mountain Resort (18.6 mi / 29.9 km)

Exploring the natural features in Stockbridge

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Stockbridge. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Naumkeag Museum (0.3 mi / 0.4 km)
  • Berkshire Botanical Garden (1.2 mi / 2 km)
  • Stockbridge Bowl (3.3 mi / 5.3 km)
  • The Mount (3.8 mi / 6.2 km)
  • Lake Mansfield Park (6.2 mi / 9.9 km)
  • Housatonic River (6.6 mi / 10.5 km)

Transport options to and around Stockbridge

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 9.6 mi (15.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 20 mi (32.3 km) away.

Frequently asked questions

What is the best area to stay in Stockbridge when booking a holiday rental?
When considering a holiday rental in Stockbridge, Massachusetts, the charming neighbourhood of Stockbridge itself is a fantastic choice. This area is steeped in history and offers a delightful blend of natural beauty and cultural attractions. One of the top highlights is the Norman Rockwell Museum, which celebrates the works of the iconic American illustrator and provides a fascinating insight into his life and art. Additionally, the serene landscape of the Berkshire Mountains surrounding Stockbridge offers ample opportunities for outdoor activities, such as hiking and enjoying scenic vistas.Another appealing area is nearby Lenox, which is just a short drive away and known for its vibrant arts scene. In Lenox, you can explore the Tanglewood Music Festival, a renowned summer venue for classical music, attracting visitors from all over. This neighbourhood also boasts lovely shops and restaurants, making it a delightful place to spend your evenings after a day of exploring.In terms of holiday rentals, Stockbridge has a variety of properties, ranging from quaint cottages to more spacious homes, allowing visitors to choose what best suits their needs.
Where are the best areas for renting a beach house in Stockbridge?
For renting a beach house in Stockbridge, the picturesque areas surrounding Stockbridge Bowl are ideal. This serene lake offers a range of holiday rentals, from charming cottages to larger family homes, all with stunning views of the water. Many properties in this area come equipped with amenities such as private docks, outdoor seating areas, and fully stocked kitchens, great for enjoying leisurely meals while taking in the natural beauty.In addition, the nearby areas of Lenox and Great Barrington provide further options for those looking to immerse themselves in the beauty of the Berkshires. Rentals here often feature spacious living areas, outdoor patios, and access to communal amenities such as swimming pools or walking trails. These towns are known for their vibrant arts scene, with local galleries and theatres, adding an enriching cultural experience to any stay.For outdoor enthusiasts, the region offers numerous hiking trails and scenic spots, with some properties allowing easy access to local parks and nature reserves.
Where are the best Stockbridge ski resort rentals?
For ski resort rentals near Stockbridge, Massachusetts, the nearby town of Lenox offers excellent options, as it is conveniently located just a short drive from the slopes at Butternut Ski Area. Many rentals in this region are charming cottages or modern homes that typically feature amenities such as fully equipped kitchens, cosy living rooms with fireplaces, and outdoor spaces for relaxation.In addition, Stockbridge itself has several quaint inns and bed-and-breakfasts that provide a more intimate lodging experience, often with beautifully appointed rooms and communal areas where guests can unwind after a day on the mountain. Some properties may include breakfast, local dining recommendations, and easy access to the cultural attractions of the Berkshires, such as Tanglewood and the Norman Rockwell Museum.For those looking to enjoy both skiing and the scenic beauty of the area, rentals in nearby Great Barrington offer a vibrant arts scene and outdoor activities. Many properties there come with amenities like hot tubs, fire pits, and proximity to local shops and restaurants, making them ideal for groups or families who want to mix leisure with adventure.
What is the most popular type of holiday rental accomodation in Stockbridge?
In Stockbridge, holiday houses are the most popular type of holiday rental, with around 88 available throughout the area. These properties are often set in picturesque surroundings, providing a charming escape for visitors. Most holiday houses come equipped with amenities such as full kitchens, spacious living areas, and outdoor spaces like decks or gardens, superb for enjoying the tranquil atmosphere. Additionally, there are about 20 cottages which offer a quaint, rustic experience, often featuring unique character and cosy interiors. For those seeking a more compact option, several condos and apartments can also be found, typically located near local attractions such as the Norman Rockwell Museum and the scenic Berkshire mountains.
Are there any family house rentals in Stockbridge?
In Stockbridge, Massachusetts, families will find a variety of holiday rentals—there are 19 available throughout the area. This picturesque town is known for its charming New England atmosphere and scenic landscapes, making it an excellent choice for family getaways. Many properties offer spacious living areas, fully equipped kitchens, and outdoor spaces where children can play and families can gather.Visitors can enjoy amenities such as Wi-Fi, air conditioning, and sometimes even features like fireplaces or patios for outdoor dining. The town is conveniently located near attractions like the Norman Rockwell Museum, which celebrates the famous artist's work, and the beautiful hiking trails of the nearby Berkshire Mountains.
Can I rent a holiday home with a pool or hot tub in Stockbridge?
In Stockbridge, Massachusetts, there are several holiday homes available for rent that feature pools or hot tubs. This picturesque town, located in the Berkshires, offers a serene setting superb for relaxation. Many of the available properties come with private pools, hot tubs, and spacious outdoor areas, ideal for enjoying the beautiful surroundings during warmer months. Inside, guests can expect well-equipped kitchens, comfortable living spaces, and amenities like Wi-Fi and air conditioning, ensuring a pleasant stay.
Are there pet-friendly house rentals in Stockbridge?
In Stockbridge, there are several pet-friendly house rentals available, making it an excellent choice for travellers looking to enjoy a getaway with their furry companions. Many of these holiday homes come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.The charming town is surrounded by beautiful natural scenery, with easy access to outdoor activities that are superb for pet owners. Nearby, the picturesque Berkshire Mountains offer a variety of trails for hiking, allowing you and your pet to explore the stunning landscapes together. Additionally, Stockbridge is close to several pet-friendly parks, giving you ample opportunities for leisurely walks and outdoor playtime.
Are there any remote work holiday rentals in Stockbridge?
In Stockbridge, Massachusetts, there are numerous holiday rentals suitable for remote work, with around 100 options available. The area is known for its picturesque New England charm and cultural heritage, making it an appealing destination for those looking to blend work and leisure. Many rentals come equipped with essential amenities such as reliable Wi-Fi, dedicated workspaces, and comfortable seating, ensuring a productive environment.Travellers will find properties ranging from quaint cottages to spacious homes, often featuring inviting living areas, fully equipped kitchens, and outdoor spaces superb for a refreshing break. The town itself offers a variety of local attractions, including art galleries and historical sites, which can provide a welcome distraction after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Stockbridge?
In Stockbridge, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties feature decks or patios, providing spaces to enjoy the beautiful surroundings. A fireplace can often be found in these rentals, creating a warm and inviting atmosphere, particularly during the cooler months. Onsite parking is typically available, making it convenient for those travelling by car. Some rentals even come with a blender, great for making smoothies or other beverages.
When is the best time to visit Stockbridge for a holiday rental?
July marks the peak season for holiday rentals in Stockbridge, where visitors flock to enjoy the charm of this picturesque Massachusetts town. This time of year is particularly vibrant, with a wealth of outdoor activities and cultural events, making it superb for those seeking a blend of relaxation and adventure. The warm summer weather, typically ranging from 15 to 30 degrees Celsius, creates an ideal environment for exploring the scenic beauty of the Berkshire Mountains or taking leisurely strolls through the lush gardens of the Norman Rockwell Museum.As the summer progresses into August and September, Stockbridge continues to thrive with tourists, offering a lively option filled with festivals and art shows. However, those looking for a quieter experience may find the low season in January to be appealing. While the winter months bring colder temperatures, averaging around -5 to 5 degrees Celsius, they also offer a serene beauty in the snow-covered landscapes, superb for cosy retreats.For travellers seeking good value, visiting Stockbridge in the early spring months of April and May can be an excellent choice. The weather is mild, and the natural beauty begins to awaken, making it a great time for hiking and enjoying the blossoming flora without the summer crowds.
What are the top attractions in Stockbridge?
In Stockbridge, visitors can enjoy a blend of natural beauty and cultural attractions. The Norman Rockwell Museum, located in the town, showcases a vast collection of the artist's works and offers insights into American culture through his lens. The picturesque Main Street is lined with charming shops and eateries, superb for a leisurely stroll.Just a short drive away, the Berkshire Botanical Garden provides a serene setting with beautiful landscaped gardens, ideal for nature lovers. For those interested in outdoor activities, the nearby Stockbridge Bowl offers opportunities for swimming, kayaking, and hiking along its scenic trails.
Are all fees included in the Stockbridge holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Stockbridge holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Stockbridge with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Stockbridge holiday homes?
You can find great discounts on holiday homes in Stockbridge on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Stockbridge holiday home booking on Bookabach?
To find Stockbridge holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Stockbridge?
A long-stay holiday home in Stockbridge is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Stockbridge holiday home?
Book your Stockbridge holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Stockbridge?
Prices for holiday homes in Stockbridge vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Stockbridge to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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