Hillsdale holiday rentals

We found 580 holiday rentals — enter your dates for availability
Discover a selection of 49 homes and other holiday rentals in Hillsdale that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Hillsdale

Showing deals for:6 Nov - 13 Nov

Queen bedroom
Terrace/patio
Property grounds
Dining room with butcher block table
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,770
for 7 nights, 1 home
AU$539 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Pool
Interior
Interior
Private kitchen
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,420
for 7 nights, 1 home
AU$631 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Second Floor Bedroom #3 - Master Suite
(see floor plans as reference)
Interior
View of dining room from living room
Living room from back staircase
Exceptional
(50 reviews)

Beautiful Berkshire Farm House on 160+ Acres

Great Barrington

8% off
AU$10,133
for 7 nights, 1 home
AU$1,448 per night
includes taxes & fees
Beautiful Berkshire Farm House on 160+ Acres
Interior
Exterior
Room
Outdoor spa tub
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,298
for 7 nights, 1 home
AU$900 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Terrace/patio
Private kitchen
Living area
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$6,195
for 7 nights, 1 home
AU$885 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Interior
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
Looking towards outside deck and tiv area in fireplace sitting area
Exceptional
(129 reviews)

Gorgeous Mountain Views Retreat: Family & Nature

Hillsdale

8% off
AU$3,858
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
Gorgeous Mountain Views Retreat: Family & Nature
Pool
Terrace/patio
Property grounds
Private kitchen
Exceptional
(5 reviews)

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

Hillsdale

8% off
AU$8,561
for 7 nights, 1 home
AU$1,223 per night
includes taxes & fees
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Interior
Property grounds
Interior
Private kitchen
Exceptional
(80 reviews)

Large Barn styled vacation home that fits groups with space to spare.

Craryville

8% off
AU$3,975
for 7 nights, 1 home
AU$568 per night
includes taxes & fees
Large Barn styled vacation home that fits groups with space to spare.
Living area
Room
Exterior
Exterior
Exceptional
(51 reviews)

Twin Maple Farm: Charming Modern Farmhouse

Great Barrington

7% off
AU$3,905
for 7 nights, 1 home
AU$558 per night
includes taxes & fees
Twin Maple Farm: Charming Modern Farmhouse
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
(6 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$7,650
for 7 nights, 1 home
AU$1,093 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Exterior
Interior
Living area
Property grounds
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,829
for 7 nights, 1 cabin
AU$547 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
View from the water
View from the Top Deck
Dining Area view
Living area
Exceptional
(10 reviews)

Lakefront +pets +skiing +bbq +firepit +games

Copake

8% off
AU$3,986
for 7 nights, 1 home
AU$569 per night
includes taxes & fees
Lakefront +pets +skiing +bbq +firepit +games
A mudroom off the back leads to the large wooden deck
You will love dining and working in this rich and colorful room
Outdoor dining and grill on the 16' x 20' wooden deck.
The living room flows into the dining room.
Exceptional
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,697
for 7 nights, 1 home
AU$671 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Dining
You, the moon, the fire pit…..,
Flat screen Smart cable tv 5G network.
WiFi of course.
2 car garage—ping pong and bikes.
Exceptional
(191 reviews)

“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway

Sheffield

8% off
AU$3,068
for 7 nights, 1 home
AU$438 per night
includes taxes & fees
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
Dining
Living area
Room
Private kitchen
Exceptional
(5 reviews)

Newley Renovated Contemporary Hudson Home 3-bedrooms 120 Acres with pond

Elizaville

8% off
AU$2,769
for 7 nights, 1 home
AU$396 per night
includes taxes & fees
Newley Renovated Contemporary Hudson Home 3-bedrooms 120 Acres with pond
Kitchen
Living Room
Property grounds
Front Gardens
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

8% off
AU$4,385
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Interior
Property grounds
Property grounds
After a day in the snow
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,580
for 7 nights, 1 home
AU$511 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Alfresco dining
River view from window
Blue House side entry from driveway
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
AU$3,545
for 7 nights, 1 home
AU$506 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Interior
Living area
Lobby
Living area
Exceptional
(7 reviews)

The Race Mountain House

Sheffield

35% off
AU$5,514
for 7 nights, 1 home
AU$788 per night
includes taxes & fees
The Race Mountain House
Private kitchen
Room
Dining
Outdoor dining
Exceptional
(31 reviews)

The Hideaway: Berkshire Home - Village of Egremont

Great Barrington

16% off
AU$3,339
for 7 nights, 1 home
AU$477 per night
includes taxes & fees
The Hideaway: Berkshire Home - Village of Egremont
Exterior
Property grounds
Living room
Coming up the path from down by the creek
Exceptional
(10 reviews)

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

Chatham

8% off
AU$2,470
for 7 nights, 1 home
AU$353 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Interior
Terrace/patio
Interior
Exterior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

Great Barrington

8% off
AU$3,439
for 7 nights, 1 cottage
AU$491 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Dining
Interior
Living area
Property grounds
Exceptional
(13 reviews)

Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

20% off
AU$4,727
for 7 nights, 1 cabin
AU$675 per night
includes taxes & fees
Guesthouse Cabin vacation rentals in Berkshire County
Room
Two Tier Decking with Grill on Lower Deck
Open Living Area
Kitchen and Dining Room
Exceptional
(14 reviews)

Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights

Hillsdale

8% off
AU$3,407
for 7 nights, 1 home
AU$487 per night
includes taxes & fees
Copake Lake Rustic All-Season 3 Bdrm, 2 Bath Home with Lake Rights
  • 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

Take in the picturesque beauty of Hillsdale

Learn about the unique charm of Hillsdale with a stay in a holiday home rental. This city's coffee shops, skiing and horse riding attract many visitors, as does its relaxing and scenic location. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Hillsdale

Are you searching for things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Hillsdale a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Catamount Ski Area (2.5 mi / 4.1 km)
  • Ski Butternut (10.5 mi / 16.9 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Umpachene Falls Park (14.3 mi / 23 km)
  • Furnace Brook Winery at Hilltop Orchards (16.5 mi / 26.6 km)
  • Wyndhurst Golf & Club (17.4 mi / 28 km)

Exploring the natural landscape of Hillsdale

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Hillsdale is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Copake Lake (4.3 mi / 7 km)
  • Lake Mansfield Park (8.3 mi / 13.4 km)
  • Housatonic River Walk (8.5 mi / 13.7 km)
  • Housatonic River (8.5 mi / 13.7 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Lake Taghkanic (11.4 mi / 18.3 km)

Travelling to and around Hillsdale

The nearest airport is in Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Hillsdale?
According to our data, houses are the most popular holiday property type in Hillsdale. But of course, everyone's idea of an awesome trip differs. Stayz has holiday homes of all sizes, shapes and budgets, so you're sure to find the perfect match.
How much does it cost to rent a holiday home in Hillsdale?
The average price for a holiday home in Hillsdale can vary depending on factors such as time of year, length of stay and property type. Whether you're searching for a sprawling villa with space for the whole family or a comfy cabin ideal for just you and the kids, just enter your dates of travel to view stays with amazing value.
How much does it cost to rent a beach house in Hillsdale?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Enter your Hillsdale travel dates to view your options on Stayz. Can't live without a hot tub, or maybe a private pool? Use the filters to select the amenities and features you want in your beach house.
Are there pet-friendly holiday homes in Hillsdale?
Yes. There are. You can pick from 60 holiday homes that allow pets in Hillsdale. Lots of our pet-friendly holiday homes come with an outdoor space for your four-legged pal to have fun in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Stayz.
Can I rent a house with a pool in Hillsdale?
Dig out your swimsuit and pool noodle, because there are 12 houses with a private pool in Hillsdale. Stay at one of these superb holiday homes and enjoy a pool day every day. Simply enter your travel dates into Stayz, then check the "pool" filter to find a place to make a splash!
What are popular home amenities in Hillsdale?
The most popular home amenities people prefer in Hillsdale are nearby museums, tennis and a nearby waterfront. Whether you're hitting the road with pals, family or even pets, Stayz holiday homes provide the best amenities for making new memories with your loved ones.
Are there large group holiday homes in Hillsdale?
With six holiday homes that can host 10 or more guests in Hillsdale, you don't have to cross anyone off the invite list. From extended family holidays to special events like birthday parties and weddings, Stayz will help you find a large group home to match the occasion.
Are there holiday homes in Hillsdale that welcome kids?
With 60 family-friendly holiday properties available in Hillsdale, now is an awesome time to introduce your kids to the magic of travel. Just check our "Properties good for families" filter box to find stays that come with amenities perfect for holidaying families, such as extra bedrooms, pools, bunk beds and entertainment units.
What are the top attractions for families in Hillsdale?
If you're holidaying with the kids, include these family-friendly attractions in Hillsdale on your list of things to do:
  • Catamount Aerial Adventure Park
  • High Falls Trail
Are there one-bedroom holiday homes in Hillsdale?
Hillsdale has 14 one-bedroom homes on offer. Often located in well-regarded areas thanks to their smaller size, a one-bedroom property is perfect if you're travelling with a buddy or your partner. And with comforts such as full kitchens and more privacy than a standard hotel, you'll be able to chill out while exploring this amazing destination.
Can I find two-bedroom holiday homes in Hillsdale?
Hillsdale has eight two-bedroom holiday homes for you to select from. Book a holiday home with all the privacy and space you need at an attractive price on Stayz.
Are there holiday homes with WiFi in Hillsdale?
You can choose from 31 holiday homes with WiFi in Hillsdale. If you'd like to disconnect from daily life on your break, but still want to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Hillsdale?
Pick your dates and then use our filters to locate holiday homes with ac in Hillsdale on Stayz. With 53 air-conditioned properties to choose from here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday home in Hillsdale?
The minimum age allowed can vary across properties on Stayz, so check the rules of the holiday home in Hillsdale you're considering. But typically, it's 16, 18 or 21.
How long can I rent a holiday home in Hillsdale for?
It's down to the Hillsdale property. To see all available options offering extended stays, just enter your travel dates and guest number into Stayz's search page. You can enjoy having the entire place to yourself, along with home comforts such as a fully-equipped kitchen and outdoor spaces to run around in. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.