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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:8 Jan - 15 Jan

Main floor open concept living area, table seating for 12, sectional couch
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 living area, seating, Roku TV, and electric fireplace to set the mood.
Exceptional
(12 reviews)

Chalet 1mi to Mount Snow with cinema and hot tub

West Dover

8% off
NZ$17,874
for 7 nights, 1 chalet
NZ$2,553 per night
includes taxes & fees
Chalet 1mi to Mount Snow with cinema and hot tub
foyer for all skiing and outdoor stuff
Jacuzzi hot tub
kitchen
main level living room sitting area
Exceptional
(26 reviews)

True Vermont Log Cabin Home at Mount Snow

West Dover

8% off
NZ$12,347
for 7 nights, 1 cabin
NZ$1,764 per night
includes taxes & fees
True Vermont Log Cabin Home at Mount Snow
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$5,109
for 7 nights, 1 chalet
NZ$730 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
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$7,563
for 7 nights, 1 chalet
NZ$1,080 per night
includes taxes & fees
New Lakefront Log Home
Second Floor - sitting area view
Clubhouse BYOB bar
June 18th 2022
Harriman Reservoir - Mt Mills East Picnic, swim and boat launch area.
Exceptional
(48 reviews)

Mountain Chalet mins to Mount Snow - Chimney Hill Resort w/indoor pool & hot tub

Wilmington

12% off
NZ$4,319
for 7 nights, 1 chalet
NZ$617 per night
includes taxes & fees
Mountain Chalet mins to Mount Snow - Chimney Hill Resort w/indoor pool & hot tub
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$6,664
for 7 nights, 1 chalet
NZ$952 per night
includes taxes & fees
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
Property grounds
Relax in the hot tub - perfect after a day on the slopes!
Interior
Living area
Exceptional
(26 reviews)

Secluded Home Near Mount Snow - 22 Acres, 4,500 sq. ft., Hot Tub, Pet-Friendly!

Brattleboro

8% off
NZ$10,441
for 7 nights, 1 home
NZ$1,492 per night
includes taxes & fees
Secluded Home Near Mount Snow - 22 Acres, 4,500 sq. ft., Hot Tub, Pet-Friendly!
Room
Living area
Dining
Terrace/patio
Exceptional
(35 reviews)

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

West Dover

8% off
NZ$15,870
for 7 nights, 1 cabin
NZ$2,267 per night
includes taxes & fees
Beautiful log home close to Mt. Snow with hot tub and sauna.
Living area
Exterior
Private kitchen
Dining
Exceptional
(39 reviews)

Beautiful Four Season Family Vacation Home

West Dover

12% off
NZ$13,772
for 7 nights, 1 home
NZ$1,967 per night
includes taxes & fees
Beautiful Four Season Family Vacation Home
Games room
Indoor spa tub
Private kitchen
Interior
Exceptional
(53 reviews)

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

Wilmington

8% off
NZ$14,556
for 7 nights, 1 home
NZ$2,079 per night
includes taxes & fees
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Outdoor dining
Interior
Private kitchen
Dining
Exceptional
(28 reviews)

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

West Dover

8% off
NZ$32,576
for 7 nights, 1 home
NZ$4,654 per night
includes taxes & fees
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
View of dining/kitchen area from entrance landing.
View from deck.
Living area
Kitchen and dining area.
Exceptional
(25 reviews)

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

Wilmington

18% off
NZ$9,593
for 7 nights, 1 home
NZ$1,370 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Living room with fireplace and 55" smart tv
Open floorplan
Fully stocked kitchen with gas range
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$10,006
for 7 nights, 1 home
NZ$1,429 per night
includes taxes & fees
Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
Large 2nd living room with foosball table, games and large smart TV
Large Kitchen will all amenities and gas fireplace.
Terrace/patio
2nd floor living room
Exceptional
(20 reviews)

Cozy & Large Only 8 minutes from Mount Snow-48 Buckboard Dr W. Dover VT

West Dover

8% off
NZ$6,777
for 7 nights, 1 home
NZ$968 per night
includes taxes & fees
Cozy & Large Only 8 minutes from Mount Snow-48 Buckboard Dr W. Dover VT
Dining
Interior
Exterior
Living area
Exceptional
(6 reviews)

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

Wilmington

8% off
NZ$13,576
for 7 nights, 1 home
NZ$1,939 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Family time!
Let the fun times begin
Open for a cold beer!
The name says it all!
Exceptional
(120 reviews)

Gather, Ski, Relax & Repeat — Spacious 6BR Vermont Getaway Overlooking the Mtns.

Wilmington

8% off
NZ$14,446
for 7 nights, 1 home
NZ$2,064 per night
includes taxes & fees
Gather, Ski, Relax & Repeat — Spacious 6BR Vermont Getaway Overlooking the Mtns.
Pool
Living area
Exterior
Property grounds
Exceptional
(23 reviews)

The Red House 3BR+Den-Shuttle, Dog Friendly,Kingswood Amenity Clubhouse, Sauna

West Dover

8% off
NZ$8,552
for 7 nights, 1 home
NZ$1,222 per night
includes taxes & fees
The Red House 3BR+Den-Shuttle, Dog Friendly,Kingswood Amenity Clubhouse, Sauna
Living area
Outdoor dining
Exterior
Property grounds
Exceptional
(31 reviews)

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

Whitingham

20% off
NZ$4,494
for 7 nights, 1 home
NZ$642 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Interior
Living area
Outdoor dining
Dining
Exceptional
(5 reviews)

Charming Home with Lake and Mountain View

Whitingham

8% off
NZ$9,705
for 7 nights, 1 cabin
NZ$1,386 per night
includes taxes & fees
Charming Home with Lake and Mountain View
Dining room (view from the kitchen)
Fully stocked renovated kitchen
View from our kitchen window in the summer
Living room with woodstove, TV, and french doors looking out to our land
Exceptional
(18 reviews)

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

Wilmington

8% off
NZ$11,935
for 7 nights, 1 home
NZ$1,705 per night
includes taxes & fees
Spruce Hill Farm - 1850 Farmhouse on 50 Acres - Minutes to Mt Snow!!
Room
Dining
Private kitchen
Living area
Exceptional
(5 reviews)

Riverside Home on Route 100 on Moover Bus Stop-3 Miles From Mount Snow

West Dover

12% off
NZ$6,199
for 7 nights, 1 home
NZ$886 per night
includes taxes & fees
Riverside Home on Route 100 on Moover Bus Stop-3 Miles From Mount Snow
Property grounds
Exterior
Pool
Interior
Very good
(6 reviews)

Crafts Inn, Hotel Suite with pool and hot tub.

Wilmington

8% off
NZ$3,090
for 7 nights, 1 room
NZ$441 per night
includes taxes & fees
Crafts Inn, Hotel Suite with pool and hot tub.
Private kitchen
Private kitchen
Living area
Interior
Exceptional
(19 reviews)

Cozy Condo Near MASS MoCA

North Adams

12% off
NZ$4,235
for 7 nights, 1 home
NZ$605 per night
includes taxes & fees
Cozy Condo Near MASS MoCA
Pool
Private kitchen
Outdoor spa tub
Amenity Center
Exceptional
(13 reviews)

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

West Dover

8% off
NZ$15,184
for 7 nights, 1 home
NZ$2,169 per night
includes taxes & fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

  • 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)
  • Jacksonville Pond (6.8 mi / 11 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)
  • Snow Lake (13.7 mi / 22 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

What is the best area to stay in Readsboro when booking a holiday rental?
When considering a holiday rental in Readsboro, Vermont, the charming neighbourhood of the village centre is an excellent choice. This area offers a quaint, picturesque atmosphere, ideal for those looking to immerse themselves in the local culture. You can find a selection of properties ranging from rustic cabins to comfortable homes, providing a variety of options to suit different tastes and budgets.Staying in the village centre places you within easy reach of some delightful attractions. One great highlight is the nearby Haystack Mountain, which offers stunning hiking opportunities and breathtaking views, great for nature enthusiasts. Additionally, the local Readsboro Community Park is a lovely spot for leisurely strolls or picnics, adding to the area's appeal.
Where are the best Readsboro ski resort rentals?
For the best ski resort rentals near Readsboro, Vermont, travellers should consider the nearby area of Wilmington, which is just a short drive away and offers convenient access to the slopes of Mount Snow. In Wilmington, you can find a range of holiday rentals, including charming chalets and spacious cabins, many of which come with amenities such as full kitchens, fireplaces, and outdoor decks great for soaking in the stunning mountain views after a day on the trails.Additionally, the village of Dover is another excellent option, featuring various lodgings that cater to ski enthusiasts. Here, you can discover properties that often include features like hot tubs, ski storage, and easy access to local dining options. Many rentals in this area are designed with comfort in mind, providing cosy living spaces where groups can relax together after a day on the slopes.For those looking to explore beyond skiing, the surrounding Green Mountain National Forest offers numerous hiking and snowshoeing trails, making it a great destination for outdoor enthusiasts year-round.
What is the most popular type of holiday rental accomodation in Readsboro?
In Readsboro, holiday houses and cottages are the most popular types of holiday rentals, with several options available. These properties are typically located in serene settings, allowing guests to enjoy the natural beauty of Vermont. Most rentals come equipped with essential amenities such as fully stocked kitchens, comfortable living areas, and outdoor spaces for relaxation. This makes them an excellent choice for families or groups looking to escape and unwind.
Are there any family house rentals in Readsboro?
In Readsboro, Vermont, there are several family-friendly house rentals available, making it a great option for those looking to explore the scenic beauty of the area. Many of these homes come with spacious living areas that provide ample room for families to gather and relax after a day of outdoor activities. You'll often find amenities such as fully equipped kitchens, where families can prepare meals together, and comfortable bedrooms.The locale is surrounded by stunning landscapes, ideal for hiking and enjoying nature. Nearby attractions like the Harriman Reservoir offer opportunities for fishing and boating, while the charming town of Wilmington is just a short drive away, featuring quaint shops and local eateries.
Are there pet-friendly house rentals in Readsboro?
In Readsboro, Vermont, there are several pet-friendly house rentals available, making it a great destination for travellers who wish to bring their furry companions along. Many of these holiday homes come equipped with amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.The area itself is surrounded by beautiful mountainous landscapes, offering opportunities for outdoor activities like hiking and exploring nature trails, which are ideal for pet owners. Additionally, the quaint charm of Readsboro provides a peaceful retreat, with easy access to local attractions and scenic vistas that enhance your stay.
Are there any remote work holiday rentals in Readsboro?
In Readsboro, Vermont, there are several holiday rentals available that cater to remote work needs. Many of these properties are equipped with reliable internet services, ensuring that guests can maintain productivity while enjoying the serene surroundings. The area is known for its picturesque landscapes, making it an ideal backdrop for those looking to blend work and leisure.Travellers can expect amenities such as spacious work areas, comfortable living spaces, and well-equipped kitchens, which are superb for preparing meals during extended stays. Additionally, some properties may offer outdoor spaces, allowing for a refreshing break during work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Readsboro?
In Readsboro, popular holiday rental amenities cater to outdoor enthusiasts and pet owners alike. Many properties are situated near hiking and biking trails, allowing guests to easily explore the stunning natural surroundings. Additionally, several rentals permit pets, making it a great choice for those travelling with furry companions. For winter sports enthusiasts, rentals in the area often provide convenient access to nearby skiing locations.
When is the best time to visit Readsboro for a holiday rental?
The best time to visit Readsboro for a holiday rental is during the peak season from August to October. This vibrant period draws visitors eager to experience the stunning autumn foliage that Vermont is famous for. As the leaves change, the landscape transforms into a kaleidoscope of colours, providing a picturesque setting for outdoor activities such as hiking and photography.August, in particular, is a popular month, offering warm temperatures ranging from 15 to 25 degrees Celsius. This is an ideal time for those who enjoy exploring the scenic trails or relaxing by the local lakes. The pleasant weather makes it comfortable for sightseeing and taking in the natural beauty that surrounds Readsboro.For travellers looking for a more budget-friendly option, February can be an appealing time to visit. While it is outside the peak season, it offers unique winter experiences such as snowshoeing and cross-country skiing, all within close reach of charming holiday rentals. Plus, the tranquil atmosphere allows for a peaceful retreat amidst the winter landscape.
What are the top attractions in Readsboro?
In Readsboro, Vermont, visitors can enjoy the natural beauty of the area, with a strong emphasis on outdoor activities. The nearby Green Mountain National Forest offers stunning hiking trails and opportunities for wildlife observation, making it a prime spot for nature enthusiasts. The scenic Deerfield River is also a highlight, ideal for kayaking, fishing, and enjoying peaceful picnic spots along its banks.For those interested in local history, the Readsboro Historical Society provides insights into the town's past and showcases various artefacts. The quaint charm of the town itself, with its classic New England architecture, creates an inviting space for visitors.In winter, Readsboro serves as a gateway to nearby ski areas, such as those found in the surrounding mountains, providing ample opportunities for skiing and snowboarding.
Are all fees included in the Readsboro holiday homes prices shown on Bookabach?
Bookabach 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 Readsboro holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Readsboro 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 Readsboro holiday homes?
You can find great discounts on holiday homes in Readsboro on Bookabach, 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 Readsboro holiday home booking on Bookabach?
To find Readsboro holiday rentals with free cancellation, just use Bookabach'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, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Readsboro?
A long-stay holiday home in Readsboro 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 Bookabach?
Bookabach'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 Readsboro holiday home?
Book your Readsboro 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Readsboro?
Prices for holiday homes in Readsboro 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. Bookabach offers something for every taste and budget, from affordable homes in Readsboro to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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 Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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 Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.