Photo by Charlie Rhodes

Spencertown holiday rentals

We found 319 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Spencertown to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Spencertown

Showing deals for:27 Nov - 4 Dec

Property grounds
Interior
Living area
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,724
for 7 nights, 1 cabin
AU$532 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Island with Kitchen drawer microwave, quartz countertops, refrigerator
Front showing deck on the side of the house in both levels
Kitchen island with 2 swivel chairs and pantry, and coat closet with barn doors
Interior
Exceptional
(133 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
AU$4,835
for 7 nights, 1 home
AU$691 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Property grounds
Terrace/patio
Games room
Private kitchen
Exceptional
(5 reviews)

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

Hillsdale

8% off
AU$9,530
for 7 nights, 1 home
AU$1,361 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Walnut dining table seats ten
Patio accessible from dining/kitchen
Double height, open kitchen and dining perfect for large vacation meals
Pool
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

7% off
AU$6,132
for 7 nights, 1 home
AU$876 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
Add a touch of warmth and charm to your dining experience!
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
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Welcome Home!
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$7,872
for 7 nights, 1 home
AU$1,125 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Dining room with butcher block table
Terrace/patio
Queen bedroom
Property grounds
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,970
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,328
for 7 nights, 1 home
AU$761 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Coming up the path from down by the creek
Property grounds
Exterior
Living room
Exceptional
(12 reviews)

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

8% off
AU$2,501
for 7 nights, 1 home
AU$357 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
dining area
River view from window
Alfresco dining
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
AU$3,482
for 7 nights, 1 home
AU$497 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
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
Welcome Home!
Open floor plan, natural light in a stylish space
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$4,031
for 7 nights, 1 home
AU$576 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Exterior
Interior
Interior
Exterior
Exceptional
(5 reviews)

Chatham Cozy Country Retreat

Chatham

7% off
AU$1,982
for 7 nights, 1 apartment
AU$283 per night
includes taxes & fees
Chatham Cozy Country Retreat
Room
Private entry is with the parking in the rear of the house.
Our combination living/dining room is a great size for four people.
Exterior
Exceptional
(24 reviews)

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

Stockbridge

24% off
AU$2,602
for 7 nights, 1 apartment
AU$372 per night
includes taxes & fees
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

  • 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

Choose a holiday rental for your Spencertown getaway

Learn about the unique charm of Spencertown with a stay in a holiday home rental. 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.

Activities and attractions in Spencertown

Do you want to discover top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Spencertown a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Catamount Ski Area (10.1 mi / 16.2 km)
  • Wyndhurst Golf & Club (12.5 mi / 20.1 km)
  • Ski Butternut (13 mi / 21 km)
  • Bousquet Ski Area (13.7 mi / 22 km)
  • Hudson Chatham Winery (6.8 mi / 10.9 km)
  • Furnace Brook Winery at Hilltop Orchards (8.5 mi / 13.8 km)

Exploring the natural landscape of Spencertown

Whether you're looking for adventure or just want to appreciate the scenery, Spencertown is a great place to spend some time outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Berkshire Botanical Garden (8.8 mi / 14.1 km)
  • Stockbridge Bowl (9.8 mi / 15.8 km)
  • Naumkeag Museum (9.9 mi / 15.9 km)
  • Lake Mansfield Park (10.3 mi / 16.5 km)
  • Housatonic River (10.8 mi / 17.5 km)
  • The Mount (11.6 mi / 18.7 km)

How to get to and around Spencertown

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 10.5 mi (16.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 13.6 mi (21.9 km) away.

Frequently asked questions

What is the best area to stay in Spencertown when booking a holiday rental?
For a delightful stay in Spencertown, New York, the area surrounding the charming village centre is an excellent choice for holiday rentals. This quaint neighbourhood is known for its picturesque landscapes and a serene atmosphere, making it great for those looking to escape the hustle and bustle of city life.While staying here, you can easily explore local attractions such as the Spencertown Academy Arts Centre, which hosts a variety of cultural events and exhibitions. The nearby scenic parks also offer beautiful walking trails, ideal for leisurely strolls amidst nature.In terms of holiday rentals, this area features a diverse selection of properties, ranging from cosy cottages to spacious homes, suiting different preferences and group sizes. The community's welcoming vibe and proximity to local amenities ensure a pleasant and convenient experience during your stay.
Where are the best Spencertown ski resort rentals?
For ski resort rentals near Spencertown, the closest skiing options can be found at Jiminy Peak, located about 30 minutes away in Hancock, Massachusetts. Visitors seeking accommodations should consider the charming town of Great Barrington, which offers a range of properties from cosy cabins to larger holiday homes suitable for families or groups. Many rentals in this area come equipped with amenities such as fireplaces, hot tubs, and fully furnished kitchens, superb for unwinding after a day on the slopes.In addition to Great Barrington, nearby towns like Lenox and Stockbridge provide further options for lodging, often featuring historic homes and modern condominiums. These properties frequently include outdoor decks, access to scenic views, and communal facilities like swimming pools or fitness centres. The cultural richness of Lenox, known for its arts scene and proximity to Tanglewood, adds a unique dimension to the stay, allowing guests to enjoy both skiing and local entertainment.Moreover, the surrounding region offers a variety of outdoor activities beyond skiing, such as hiking trails in the nearby Berkshire Mountains and opportunities for snowshoeing or cross-country skiing.
What is the most popular type of holiday rental accomodation in Spencertown?
In Spencertown, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically provide a spacious environment, ideal for families or groups, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas. Many also come with outdoor spaces such as gardens or patios, superb for enjoying the serene surroundings.
Are there any family house rentals in Spencertown?
In Spencertown, New York, there are several family-friendly house rentals available, making it an appealing option for those seeking a getaway. This charming area offers a mix of spacious homes, often featuring amenities such as well-equipped kitchens, ample living spaces for gathering, and outdoor areas superb for children to play.Visitors can explore the nearby natural beauty of the Berkshires, with opportunities for hiking and enjoying the picturesque landscapes. The local community is also home to quaint shops and delightful dining options, ensuring a well-rounded experience for families.
Are there pet-friendly house rentals in Spencertown?
In Spencertown, 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 gardens, outdoor seating areas, and fully equipped kitchens, allowing for a comfortable and convenient stay. Properties often feature cosy living spaces, multiple bedrooms, and sometimes even additional facilities like fire pits or barbecues for entertaining.The surrounding area offers various opportunities for outdoor exploration with pets. Nearby parks and natural spaces provide ample room for walks and playtime.
Are there any remote work holiday rentals in Spencertown?
In Spencertown, New York, there are several holiday rentals that cater to remote workers, making it an ideal spot for those looking to blend work with a rural retreat. Many properties offer essential amenities such as complimentary Wi-Fi, dedicated desk spaces, and comfortable living areas that support productivity.The charming town is surrounded by picturesque landscapes, providing a serene environment for work and relaxation. Visitors can enjoy nearby points of interest, including local parks and hiking trails, superb for unwinding after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Spencertown?
In Spencertown, popular rental amenities include features that enhance comfort and convenience during a stay. Many holiday rentals come equipped with a deck or patio, allowing guests to enjoy the serene surroundings outdoors. Air conditioning is commonly available, ensuring a pleasant atmosphere, especially during warmer months. Travellers can also expect to find coffee and tea makers in most properties, superb for those who appreciate a warm beverage in the morning. Additionally, a desk is often provided, suiting those who may need to attend to work or personal tasks while away. Onsite parking is another amenity that adds to the convenience, making it easier for guests to explore the beautiful countryside of the area.
When is the best time to visit Spencertown for a holiday rental?
The peak season for visiting Spencertown is during the summer months of June to August, with July being particularly popular among travellers. This vibrant period invites visitors to partake in outdoor activities, explore local farms, and enjoy the picturesque landscapes that define this charming area. The warm weather, with temperatures typically ranging from 15 to 30 degrees Celsius, creates an ideal setting for hiking and enjoying local festivals.If you're seeking a more tranquil experience, consider visiting in October. This month offers a beautiful display of autumn foliage, making it superb for leisurely strolls and scenic drives through the stunning countryside. The cooler temperatures, usually between 5 and 15 degrees Celsius, provide a refreshing atmosphere for outdoor exploration without the summer crowds.
What are the top attractions in Spencertown?
In Spencertown, New York, visitors can enjoy a quaint and picturesque rural setting with several attractions that highlight the area's natural beauty and cultural heritage. The surrounding Columbia County is known for its scenic landscapes, making it ideal for outdoor enthusiasts. The nearby Catamount Ski Area offers winter sports activities, while the summer months are superb for hiking and exploring the lush trails in the Berkshires.Spencertown is also home to the Spencertown Academy Arts Council, which hosts various art exhibitions, performances, and community events throughout the year. The charming local architecture and historic buildings provide a glimpse into the area's past, and the nearby farms and markets offer fresh local produce and artisanal goods.
Are all fees included in the Spencertown 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 Spencertown holiday homes with parking?
Stayz offers a wide selection of holiday homes in Spencertown 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 Spencertown holiday homes?
You can find great discounts on holiday homes in Spencertown 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 Spencertown holiday home booking on Stayz?
To find Spencertown 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 Spencertown?
A long-stay holiday home in Spencertown 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 Spencertown holiday home?
Book your Spencertown 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 Spencertown?
Prices for holiday homes in Spencertown 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 Spencertown 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.