Southfield holiday rentals

We found 288 holiday rentals — enter your dates for availability
Discover a selection of 9 homes and other holiday rentals in Southfield that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday rentals have the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Southfield

Showing deals for:11 Dec - 18 Dec

Terrace/patio
House facing lake with deck above, canoe and kayak stored on ground level.
View of lake through window, table for 6 on right, 4 bar stools at counter
Stairway to landing with one LR couch, barstools, kitchen in background
Exceptional
(169 reviews)

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis

16% off
AU$2,679
for 7 nights, 1 home
AU$383 per night
includes taxes & fees
4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
Exterior
Terrace/patio
Interior
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,374
for 7 nights, 1 cottage
AU$482 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Living area
Private kitchen
Living area
Exterior
Exceptional
(9 reviews)

Luxurious Mountain Retreat - Private 40-Acre Family Haven

Sheffield

8% off
AU$8,935
for 7 nights, 1 home
AU$1,276 per night
includes taxes & fees
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Staircase
You will love dining and working in this rich and colorful room
The living room flows into the dining room.
Outdoor dining and grill on the 16' x 20' wooden deck.
Exceptional
(42 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,806
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Kitchen open to living room
Kitchen
Cottage Entrance
2nd bedroom
Exceptional
(78 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
AU$2,266
for 7 nights, 1 cottage
AU$324 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Living area
Interior
Private kitchen
Pool
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,336
for 7 nights, 1 home
AU$619 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Private kitchen
Welcome Home!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$3,958
for 7 nights, 1 home
AU$565 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
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
AU$4,867
for 7 nights, 1 home
AU$695 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
Truly nestled on 5+ acres and LESS than 0.8miles to downtown Great Barrington
Seamless entertaining with the wide open concept, living room -kitchen- patio
Exceptional
(28 reviews)

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

Great Barrington

6% off
AU$5,572
for 7 nights, 1 home
AU$796 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
Interior
Living area
Living area
Living area
Excellent
(9 reviews)

The Race Mountain House

Sheffield

35% off
AU$5,305
for 7 nights, 1 home
AU$758 per night
includes taxes & fees
The Race Mountain House
Property grounds
Property grounds
After a day in the snow
Interior
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,445
for 7 nights, 1 home
AU$492 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Outdoor dining
Room
Dining
Private kitchen
Exceptional
(33 reviews)

The Hideaway: Berkshire Home - Village of Egremont

egremont

16% off
AU$3,276
for 7 nights, 1 home
AU$468 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Exterior
Interior
Living area
Private kitchen
Exceptional
(60 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,630
for 7 nights, 1 apartment
AU$233 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Property grounds
Interior
Dining
Living area
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

21% off
AU$4,547
for 7 nights, 1 cabin
AU$650 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County
Game, puzzle and play table - plenty of chairs.
Porch opens up from dining room. Ceiling fan and lights above.
Come and unwind.
View of the river.
Exceptional
(43 reviews)

Converted Berkshire schoolhouse on a quiet river

New Marlborough

8% off
AU$2,798
for 7 nights, 1 home
AU$400 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river
Private kitchen
Exterior
Room
Private kitchen
Exceptional
(5 reviews)

Luxury on the River near Tanglewood w/220 EV Charge

Sandisfield

8% off
AU$2,846
for 7 nights, 1 home
AU$407 per night
includes taxes & fees
Luxury on the River near Tanglewood w/220 EV Charge
Room
Outdoor dining
Dining
Exterior detail
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
AU$3,850
for 7 nights, 1 home
AU$550 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Private kitchen
Outdoor dining
Exterior
Private kitchen
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
AU$3,849
for 7 nights, 1 home
AU$550 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Interior
Front Entrance
dining room
Interior
Exceptional
(15 reviews)

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Sheffield

8% off
AU$5,935
for 7 nights, 1 home
AU$848 per night
includes taxes & fees
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
View from Kitchen
Dining room
Front view of house
living room
Exceptional
(37 reviews)

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont

8% off
AU$4,085
for 7 nights, 1 home
AU$584 per night
includes taxes & fees
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Room
Property grounds
Exterior
Interior
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
AU$1,949
for 7 nights, 1 apartment
AU$278 per night
includes taxes & fees
The Serendipity Spot
Interior
Living area
Private kitchen
Bathroom
Exceptional
(7 reviews)

Comfortable, renovated 2 bedroom apartment in historic grist mill.

SOUTH EGREMONT

16% off
AU$2,549
for 7 nights, 1 apartment
AU$364 per night
includes taxes & fees
Comfortable, renovated 2 bedroom apartment in historic grist mill.
Private kitchen
Living area
Outdoor dining
Room
Exceptional
(7 reviews)

Lakeville Lodge with Private Pool – Walkable to Lake, Restaurants, & Salisbury!

Salisbury

8% off
AU$5,073
for 7 nights, 1 home
AU$725 per night
includes taxes & fees
Lakeville Lodge with Private Pool – Walkable to Lake, Restaurants, & Salisbury!

  • 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

Travel to adventurous Southfield

The parks and other outdoor surroundings create an inviting atmosphere in Southfield. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Southfield

Do you want to find attractions to see during your stay? Venture out of your holiday home and experience everything that makes Southfield a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (7.2 mi / 11.6 km)
  • Otis Ridge (9.4 mi / 15.1 km)
  • Catamount Ski Area (13.4 mi / 21.5 km)
  • Wyndhurst Golf & Club (16.8 mi / 27 km)
  • Mohawk Mountain Ski Area (18.8 mi / 30.2 km)
  • Umpachene Falls Park (2.1 mi / 3.3 km)

Exploring the natural features in Southfield

Whether you're looking for adventure or just want to appreciate the scenery, Southfield is a great place to get out in nature. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Lake Buel (5.2 mi / 8.3 km)
  • Housatonic River (9.3 mi / 15 km)
  • Housatonic River Walk (9.3 mi / 15 km)
  • Lake Mansfield Park (9.9 mi / 15.9 km)
  • Otis Reservoir (10.4 mi / 16.8 km)
  • Great Falls (11.9 mi / 19.2 km)

Transport options to and around Southfield

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 22.6 mi (36.3 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Westfield, MA (BAF-Barnes Municipal), which is 26.8 mi (43.1 km) away.

Frequently asked questions

What is the best area to stay in Southfield when booking a holiday rental?
When considering a holiday rental in Southfield, Massachusetts, one of the best areas to explore is the neighbourhood surrounding the vibrant parks and recreational spaces. This area offers a charming blend of natural beauty and community spirit, making it an inviting choice for visitors.Nearby, you'll find delightful attractions such as the expansive parkland that features walking trails, picnic spots, and playgrounds, superb for families or those seeking a leisurely day outdoors. Additionally, the local cultural centre hosts various events and activities throughout the year, providing a wonderful opportunity to engage with the community.While the number of holiday rentals can vary, there are generally a good selection of properties available in this area, suiting different preferences and budgets.
Where are the best Southfield ski resort rentals?
For ski resort rentals near Southfield, Massachusetts, the closest ski areas are located in the nearby Berkshires, particularly around towns like Pittsfield and Lenox. In these areas, travellers can find a variety of accommodations ranging from cozy chalets to larger family homes, many of which come equipped with essential amenities such as fully stocked kitchens, fireplaces, and outdoor spaces for relaxation after a day on the slopes.In Pittsfield, for instance, visitors may find rentals that offer proximity to Bousquet Mountain, where skiing and snowboarding can be enjoyed. Properties in this area often have features like ski storage, hot tubs, and easy access to local dining and shopping options, making them convenient for both winter sports enthusiasts and families.Lenox, known for its cultural offerings and beautiful landscapes, also provides an excellent base for skiing, with its charming inns and holiday homes. Many rentals here include amenities such as game rooms, spacious living areas, and access to nearby hiking trails, which can be particularly appealing during the off-season.
What is the most popular type of holiday rental accomodation in Southfield?
In Southfield, holiday houses are the most popular type of holiday rental, with several available throughout the area. These homes typically offer spacious living arrangements, often featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas for relaxation. Many also include outdoor spaces, great for enjoying the natural surroundings. In addition to holiday houses, there are also several cabins and cottages, which provide a more rustic and cosy atmosphere, often set in serene locations ideal for a peaceful getaway.
Are there any family house rentals in Southfield?
In Southfield, Massachusetts, there are several family-friendly holiday rentals available, making it a suitable destination for groups. Visitors can find properties that offer spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play. Many homes also feature amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.The town is located near various parks and recreational areas, providing opportunities for family outings and outdoor activities.
Can I rent a holiday home with a pool or hot tub in Southfield?
In Southfield, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs. This suburban area provides a peaceful environment while still being conveniently located near various attractions and amenities. Travellers can expect properties equipped with private pools, hot tubs, spacious outdoor areas, and fully stocked kitchens, making them ideal for relaxation and family gatherings. Some rentals may also include additional comforts such as Wi-Fi, air conditioning, and backyard spaces for outdoor activities.
Are there pet-friendly house rentals in Southfield?
In Southfield, Massachusetts, there are several pet-friendly house rentals available, offering a welcoming environment for those travelling with pets. Many of these rentals feature amenities such as spacious living areas, fully equipped kitchens, and private outdoor spaces where pets can enjoy the fresh air. The homes are often situated in tranquil settings, providing a peaceful retreat for families and groups.While Southfield itself is a quiet area, it is surrounded by beautiful landscapes ideal for outdoor activities. Nearby parks and nature reserves offer opportunities for leisurely walks and exploration, making it a suitable destination for pet owners looking to enjoy the great outdoors.
Are there any remote work holiday rentals in Southfield?
In Southfield, Massachusetts, there are about 10 remote work-friendly holiday rentals available. This area offers a range of properties equipped to support remote working needs, featuring reliable internet access and Wi-Fi, ensuring that guests can stay connected. Many rentals also provide comfortable workspaces, allowing for a productive environment away from home.Located in a picturesque setting, these properties often include additional amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces for relaxation. The nearby attractions, including parks and natural reserves, provide opportunities for leisure activities, making it a well-rounded destination for those blending work and relaxation. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Southfield?
In Southfield, popular rental amenities include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces to relax and enjoy the surroundings. Fireplaces are a common addition, adding a cosy touch, especially during cooler months. Onsite parking is typically available, making it convenient for those travelling by car. Additionally, some rentals come with porches or lanais, offering further opportunities to unwind outside.
What are the top attractions in Southfield?
In Southfield, Massachusetts, visitors can explore a variety of attractions that highlight the area's natural beauty and community spirit. One of the main draws is the Southfield Park, which offers walking trails, playgrounds, and picnic areas, making it a great spot for families and outdoor enthusiasts. The park's open spaces are great for leisurely strolls and enjoying the serene environment.Additionally, the Southfield Plaza provides shopping and dining options, allowing visitors to experience local cuisine and retail. For history enthusiasts, the nearby Southfield Historical Society features exhibits that showcase the town's rich history and heritage.Nature lovers may also enjoy the proximity to the scenic trails and waterways in the surrounding areas, making it an excellent base for outdoor activities.
Are all fees included in the Southfield holiday homes prices shown on Stayz?
Stayz 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 Southfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Southfield 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 Southfield holiday homes?
You can find great discounts on holiday homes in Southfield on Stayz, 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 Southfield holiday home booking on Stayz?
To find Southfield holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Southfield?
A long-stay holiday home in Southfield 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 Stayz?
Stayz'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 Southfield holiday home?
Book your Southfield 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Southfield?
Prices for holiday homes in Southfield 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. Stayz offers something for every taste and budget, from affordable homes in Southfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.