Photo by Charlie Rhodes

Spencertown holiday homes

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

Dining
Interior
Exterior
Living area
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,606
for 7 nights, 1 cabin
NZ$658 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Games room
Terrace/patio
Pool
Property grounds
Exceptional
(5 reviews)

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

Hillsdale

7% off
NZ$12,065
for 7 nights, 1 home
NZ$1,724 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
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
Kitchen island with 2 swivel chairs and pantry, and coat closet with barn doors
Exceptional
(133 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
NZ$5,866
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Walnut dining table seats ten
Patio accessible from dining/kitchen
Pool
Double height, open kitchen and dining perfect for large vacation meals
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

7% off
NZ$7,498
for 7 nights, 1 home
NZ$1,071 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
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
Add a touch of warmth and charm to your dining experience!
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$9,671
for 7 nights, 1 home
NZ$1,382 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Screened in porch
Terrace/patio
Property grounds
Dining room with butcher block table
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,910
for 7 nights, 1 home
NZ$701 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Property grounds
Interior
Interior
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,536
for 7 nights, 1 home
NZ$934 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Living room
Property grounds
Living room
Coming up the path from down by the creek
Exceptional
(12 reviews)

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

Chatham

8% off
NZ$3,008
for 7 nights, 1 home
NZ$430 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Alfresco dining
River view from window
dining area
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
NZ$4,221
for 7 nights, 1 home
NZ$603 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Open floor plan, natural light in a stylish space
Ultimate Relaxation!  The hot tub will be warm and waiting for your arrival
Welcome Home!
Private kitchen
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
NZ$4,980
for 7 nights, 1 home
NZ$711 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Interior
Interior
Exterior
Room
Exceptional
(5 reviews)

Chatham Cozy Country Retreat

Chatham

8% off
NZ$2,350
for 7 nights, 1 apartment
NZ$336 per night
includes taxes & fees
Chatham Cozy Country Retreat
Exterior
Private entry is with the parking in the rear of the house.
Our combination living/dining room is a great size for four people.
Room
Exceptional
(24 reviews)

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

Stockbridge

24% off
NZ$3,130
for 7 nights, 1 apartment
NZ$447 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 most popular type of holiday home accommodation in Spencertown?
The most in-demand types of holiday homes in Spencertown are hotel suites. After something a little different? Bookabach offers a variety of options to match our guests' diverse needs, so you'll see holiday homes in lots of sizes and shapes. The ideal home away from home is waiting for you — grab yours today.
How much does it cost to rent a holiday home in Spencertown?
Length of stay, season and property type are some of the conditions that can influence the price of a holiday home. Simply add your dates of travel to find your ideal escape. From homey country cottages to sprawling luxury villas, all Bookabach holiday homes provide incredible value.
How much does it cost to rent a beach house in Spencertown?
The average price for a holiday home by the beach in Spencertown depends on when you're going and the style and size of property you want. You can quickly and easily find prices on Bookabach by entering your preferred travel dates. Then use our filters to choose the number of bedrooms and amenities that you need, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in Spencertown?
With five holiday homes that allow pets, your furry buddy can join in on your Spencertown break. Use our filter tool to search our pet-friendly holiday homes and find a stay that'll set tails wagging on Bookabach.
What are popular home amenities in Spencertown?
When it comes to home amenities that guests are on the lookout for in Spencertown, high-speed internet services, free WiFi and off-street parking options are the most popular. With Bookabach holiday homes, there are options to suit your style and taste, whether you're going away with friends, family or even pets.
Are there holiday homes in Spencertown that welcome kids?
Spencertown has five family-friendly holiday homes to pick from. And tracking down a stay that welcomes kiddos is super easy with Bookabach's "Properties good for families" filter. As well as having the entire place to yourselves, you'll get perks and amenities like dining rooms, kitchens and yards.
What are the top attractions for families in Spencertown?
There are loads of fabulous things to see and do with the family in Spencertown, including:
  • Catamount Aerial Adventure Park
  • High Falls Trail
  • Omi International Arts Centre
Are there one-bedroom holiday homes in Spencertown?
Spencertown has four one-bedroom homes available. Typically situated in well-regarded areas due to their smaller size, a one-bedroom holiday home is great if you're travelling with a friend or your partner. And with comforts such as kitchens and more privacy than a standard hotel, you'll be able to relax while discovering this exciting destination.
Are there holiday homes with WiFi in Spencertown?
Whether you'd like to keep up with the headlines, write a few emails or update your social media, there are five holiday homes with WiFi in Spencertown. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Spencertown?
Spencertown has four holiday homes where you'll be able to unwind in air-conditioned comfort. To locate a property on Bookabach that provides this perk, enter your dates of travel and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Spencertown?
You'll have to check with the Spencertown holiday property you're considering on Bookabach as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Spencertown for?
It's down to the Spencertown property. To look over a list of options offering extended stays, just type your travel dates and guest number into Bookabach's search page. You can enjoy having the whole property to yourself, as well as amenities such as a fully-equipped kitchen and a yard to play in. Be on the lookout for any long-term stays that offer weekly or monthly discounts.