Photo by Free Love Hippie

Readsboro holiday homes

We found 835 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Readsboro that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as a hot tub and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Readsboro

Showing deals for:11 Dec - 18 Dec

Silestone counter top and Hickory cabinets
A beautiful brook that runs through our lot
Master 2 Second Floor
Enjoy chess, checkers or backgammon
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
NZ$7,202
for 7 nights, 1 chalet
NZ$1,029 per night
includes taxes & fees
New Lakefront Log Home
Interior
Large living room with endless natural light
New custom kitchen
Property grounds
Exceptional
(17 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

West Dover

8% off
NZ$18,994
for 7 nights, 1 chalet
NZ$2,713 per night
includes taxes & fees
Private 6 bedroom Chalet 5min to Mt Snow
Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Terrace/patio
Exterior
Sun or snow, it's quite the show
Exceptional
(10 reviews)

HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake

Wilmington

15% off
NZ$5,125
for 7 nights, 1 chalet
NZ$732 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Main living area, seating, Roku TV, and electric fireplace to set the mood.
The NEW back deck with dining table, hot tub, and charcoal grill for cooking
Updated ski chalet, in the mountains of southern Vermont, 1 minute from Mt Snow
Main floor open concept living area, table seating for 12, sectional couch & TV
Exceptional
(12 reviews)

Chalet 1mi to Mount Snow with cinema and hot tub

West Dover

7% off
NZ$8,188
for 7 nights, 1 chalet
NZ$1,170 per night
includes taxes & fees
Chalet 1mi to Mount Snow with cinema and hot tub
Room
Living area
Private kitchen
Terrace/patio
Exceptional
(35 reviews)

Beautiful log home close to Mt. Snow with hot tub and sauna.

West Dover

7% off
NZ$12,315
for 7 nights, 1 cabin
NZ$1,759 per night
includes taxes & fees
Beautiful log home close to Mt. Snow with hot tub and sauna.
View from Kitchen sink
View out front door
Early morning summer view
 Open Kitchen with a wide open feel
Exceptional
(243 reviews)

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews

Wilmington

8% off
NZ$8,588
for 7 nights, 1 home
NZ$1,227 per night
includes taxes & fees
Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews
Enjoy the infamous Moss Rock!
Kitchen and dining area.
Living area with wood stove.
Living area with wood stove
Exceptional
(26 reviews)

Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington

West Dover

8% off
NZ$6,410
for 7 nights, 1 chalet
NZ$916 per night
includes taxes & fees
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
King bed
Front of the house
Fully equipped kitchen
Patio chairs and solo stove firepit
Exceptional
(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

7% off
NZ$3,750
for 7 nights, 1 chalet
NZ$536 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Outdoor dining
Living area
Living area
Master bedroom to the left of kitchen. Entryway and den to the right.
Exceptional
(113 reviews)

Spacious, Comfortable & Close!!! GOLF TRIPS!

West Dover

15% off
NZ$9,601
for 7 nights, 1 home
NZ$1,372 per night
includes taxes & fees
Spacious, Comfortable & Close!!! GOLF TRIPS!
foyer for all skiing and outdoor stuff
Jacuzzi hot tub
main level living room sitting area
main level living room area
Exceptional
(26 reviews)

True Vermont Log Cabin Home at Mount Snow

West Dover

8% off
NZ$11,651
for 7 nights, 1 cabin
NZ$1,664 per night
includes taxes & fees
True Vermont Log Cabin Home at Mount Snow
Games room
Exterior
Private kitchen
Dining
Exceptional
(39 reviews)

Beautiful Four Season Family Vacation Home

West Dover

12% off
NZ$12,315
for 7 nights, 1 home
NZ$1,759 per night
includes taxes & fees
Beautiful Four Season Family Vacation Home
Dining
Indoor spa tub
Games room
Interior
Exceptional
(53 reviews)

SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.

Wilmington

8% off
NZ$14,143
for 7 nights, 1 home
NZ$2,020 per night
includes taxes & fees
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Living area
Interior
Private kitchen
Exterior
Exceptional
(6 reviews)

Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!

Wilmington

7% off
NZ$13,233
for 7 nights, 1 home
NZ$1,890 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Dining
Photo by @dirtandglass
Enjoy the family friendly open concept living area with soaring ceilings
Gather to enjoy the cozy wood burning fireplace with 65” TV/ DVD player/ movies
Exceptional
(30 reviews)

Mount Snow Chalet-modern family home, chefs kitchen, gameroom, Clubhouse pool

Wilmington

8% off
NZ$8,999
for 7 nights, 1 home
NZ$1,286 per night
includes taxes & fees
Mount Snow Chalet-modern family home, chefs kitchen, gameroom, Clubhouse pool
Private kitchen
Interior
Outdoor dining
Dining Room Table accommodating 10 to 12 guests comfortably
Exceptional
(28 reviews)

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

West Dover

8% off
NZ$31,000
for 7 nights, 1 home
NZ$4,429 per night
includes taxes & fees
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Room
View from deck.
Living area
View of dining/kitchen area from entrance landing.
Exceptional
(25 reviews)

Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.

Wilmington

18% off
NZ$9,084
for 7 nights, 1 home
NZ$1,298 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Living area
Private kitchen
Pool
Outdoor spa tub
Exceptional
(13 reviews)

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

West Dover

7% off
NZ$8,294
for 7 nights, 1 home
NZ$1,185 per night
includes taxes & fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Living area
Outdoor dining
Property grounds
Living area
Exceptional
(31 reviews)

Secluded large country home for big groups with giant open yard for outdoor fun.

Whitingham

20% off
NZ$4,281
for 7 nights, 1 home
NZ$612 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Living area
Private kitchen
Room
Interior
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$4,034
for 7 nights, 1 home
NZ$576 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Outdoor firepit with plenty of seating
Open floorplan
Living room with fireplace and 55" smart tv
downtown is just a 4 minute walk. So much to see and do
Exceptional
(11 reviews)

Large rustic home with gameroom. Near lakes, skiing, walk to downtown.

Wilmington

12% off
NZ$7,830
for 7 nights, 1 home
NZ$1,119 per night
includes taxes & fees
Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
Inside Clubhouse
Exterior
Living area
Dining
Exceptional
(24 reviews)

Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow

Wilmington

8% off
NZ$5,277
for 7 nights, 1 home
NZ$754 per night
includes taxes & fees
Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow
Living room with woodstove, TV, and french doors looking out to our land
Fully stocked renovated kitchen
View from our land in the back
View from our kitchen window in the summer
Exceptional
(18 reviews)

Spruce Hill Farm - 1850 Farmhouse on 50 Acres - Minutes to Mt Snow!!

Wilmington

8% off
NZ$11,165
for 7 nights, 1 home
NZ$1,595 per night
includes taxes & fees
Spruce Hill Farm - 1850 Farmhouse on 50 Acres - Minutes to Mt Snow!!
Living room overlooks the back fields and sunset views
View from dining room into kitchen with fireplace
Main living room with beamed ceilings
Bright sunny kitchen
Exceptional
(34 reviews)

Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Jacksonville

8% off
NZ$8,354
for 7 nights, 1 home
NZ$1,193 per night
includes taxes & fees
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Room
Owner and guest parking. Private guest access is located through the porch door.
Hallway view from the bathroom looking toward the kitchen area.
A small kitchenette fully equipped for small-scale cooking.
Exceptional
(34 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
NZ$1,387
for 7 nights, 1 apartment
NZ$198 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
  • 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

Book a holiday rental for your Readsboro getaway

Learn about the unique charm of Readsboro with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Readsboro

Do you want to find attractions to visit in the area? Venture out of your holiday home and check out everything that makes Readsboro 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:

  • The Hermitage Golf Club (9.3 mi / 15 km)
  • Prospect Mountain Cross-Country Ski Center (9.5 mi / 15.3 km)
  • The Hermitage Club (10.7 mi / 17.2 km)
  • Berkshire East Ski Resort (11.3 mi / 18.2 km)
  • Mount Snow Golf Course (12.2 mi / 19.6 km)
  • Mount Snow (13.1 mi / 21.1 km)

Exploring the natural landscape of Readsboro

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

  • Harriman Reservoir (4.7 mi / 7.5 km)
  • Lake Raponda (9.7 mi / 15.6 km)
  • Windsor Lake Park (9.7 mi / 15.6 km)
  • Hogback Mountain Conservation Area (9.9 mi / 15.9 km)
  • Mount Greylock (14.5 mi / 23.3 km)
  • Mount Greylock State Reservation (14.9 mi / 24 km)

Transport to and around Readsboro

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 29.7 mi (47.7 km) from the city centre.

Frequently asked questions

How much does it cost to rent a holiday home in Readsboro?
Length of stay, season and property type are some factors that can influence the price of a holiday home. Simply click on your dates of travel to find your dream escape. From cosy country cottages to sprawling villas, all Bookabach holiday homes provide amazing value.
How much does it cost to rent a beach house in Readsboro?
When you travel and the size and style of the property will help determine the cost of your beachside escape. Put in your Readsboro travel dates to see your options on Bookabach. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the features and amenities you want.
How old do you have to be to rent a holiday home in Readsboro?
You'll have to check with the Readsboro holiday home you'd like on Bookabach as the minimum age varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Readsboro for?
It really depends on the Readsboro property. To browse a list of options offering extended stays, just type your dates and guest number into Bookabach's search page. Look forward to having the entire property to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and a backyard to run around in. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.