Whitingham holiday homes

We found 677 holiday rentals — enter your dates for availability
Discover a selection of 14 homes and other holiday rentals in Whitingham that are perfect for your trip. Whether you’re staying in a holiday home with family or friends, you'll have the amenities that you expect and more, which might include a hot tub and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Whitingham

Showing deals for:18 Dec - 25 Dec

Two story living room with 70" smarttv, premium directtv and bluetooth turntable
Terrace/patio
Sun or snow, it's quite the show
Indoor hot tub
Exceptional
(10 reviews)

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

Wilmington

16% off
NZ$10,304
for 7 nights, 1 chalet
NZ$1,472 per night
includes taxes & fees
HotTub&GameRm&Traeger Smoker-15 min 2 Mt Snow, Across from Golf, 5 min to Lake
Exterior
Large living room with endless natural light
Interior
New custom kitchen
Exceptional
(17 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

West Dover

8% off
NZ$19,751
for 7 nights, 1 chalet
NZ$2,822 per night
includes taxes & fees
Private 6 bedroom Chalet 5min to Mt Snow
Master 2 Second Floor
A beautiful brook that runs through our lot
Summer view from the lake
Enjoy chess, checkers or backgammon
Exceptional
(101 reviews)

New Lakefront Log Home

Wilmington

12% off
NZ$7,282
for 7 nights, 1 chalet
NZ$1,040 per night
includes taxes & fees
New Lakefront Log Home
Private kitchen
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$15,406
for 7 nights, 1 cabin
NZ$2,201 per night
includes taxes & fees
Beautiful log home close to Mt. Snow with hot tub and sauna.
King bed
Front of the house
Patio chairs and solo stove firepit
Fully equipped kitchen
Exceptional
(16 reviews)

Chalet Mount Snow/Stratton Skiing/hiking

East Dover

8% off
NZ$5,987
for 7 nights, 1 chalet
NZ$855 per night
includes taxes & fees
Chalet Mount Snow/Stratton Skiing/hiking
Dining area, 10 Chairs are now black, Need a new picture!
View out front door
Open Kitchen with a wide open feel
View from Kitchen sink
Exceptional
(243 reviews)

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

Wilmington

8% off
NZ$9,143
for 7 nights, 1 home
NZ$1,306 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.
Dry your ski gear on the hooks near the warm wood stove.
Exceptional
(26 reviews)

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

West Dover

8% off
NZ$6,822
for 7 nights, 1 chalet
NZ$975 per night
includes taxes & fees
Vermont ski chalet near beautiful Mount Snow and the quaint town of Wilmington
Private kitchen
Exterior
Games room
Living area
Exceptional
(39 reviews)

Beautiful Four Season Family Vacation Home

West Dover

12% off
NZ$13,698
for 7 nights, 1 home
NZ$1,957 per night
includes taxes & fees
Beautiful Four Season Family Vacation Home
foyer for all skiing and outdoor stuff
Jacuzzi hot tub
main level living room sitting area
kitchen
Exceptional
(26 reviews)

True Vermont Log Cabin Home at Mount Snow

West Dover

8% off
NZ$11,779
for 7 nights, 1 cabin
NZ$1,683 per night
includes taxes & fees
True Vermont Log Cabin Home at Mount Snow
Exterior
Interior
Dining
Private kitchen
Exceptional
(6 reviews)

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

Wilmington

7% off
NZ$13,379
for 7 nights, 1 home
NZ$1,911 per night
includes taxes & fees
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Private kitchen
Indoor spa tub
Dining
Interior
Exceptional
(53 reviews)

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

Wilmington

8% off
NZ$14,299
for 7 nights, 1 home
NZ$2,043 per night
includes taxes & fees
SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
View of dining/kitchen area from entrance landing.
View from deck.
Kitchen and dining area.
Room
Exceptional
(25 reviews)

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

Wilmington

18% off
NZ$9,185
for 7 nights, 1 home
NZ$1,312 per night
includes taxes & fees
Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Fully stocked kitchen with gas range
Open floorplan
Outdoor firepit with plenty of seating
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$11,994
for 7 nights, 1 home
NZ$1,713 per night
includes taxes & fees
Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
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$4,329
for 7 nights, 1 home
NZ$618 per night
includes taxes & fees
Secluded large country home for big groups with giant open yard for outdoor fun.
Dining room (view from the kitchen)
Fully stocked renovated kitchen
Living room with woodstove, TV, and french doors looking out to our land
View from our land in the back
Exceptional
(18 reviews)

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

Wilmington

8% off
NZ$11,288
for 7 nights, 1 home
NZ$1,613 per night
includes taxes & fees
Spruce Hill Farm - 1850 Farmhouse on 50 Acres - Minutes to Mt Snow!!
Exterior detail
Owner and guest parking. Private guest access is located through the porch door.
Hallway view from the bathroom looking toward the kitchen area.
Room
Exceptional
(34 reviews)

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

8% off
NZ$1,688
for 7 nights, 1 apartment
NZ$241 per night
includes taxes & fees
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Privacy personified at the Cottage. Enjoy simple country sophistication.
Living area
Room
Interior
Exceptional
(211 reviews)

Amazing People & Pet-Welcoming Country Haven

Shelburne Falls

9% off
NZ$2,274
for 7 nights, 1 room
NZ$325 per night
includes taxes & fees
Amazing People & Pet-Welcoming Country Haven
fire pit
MassMoCA in nearby North Adams, Mass
Living room
Dining room
Exceptional
(13 reviews)

Family Home in the mountains. Get out and explore!

Monroe

16% off
NZ$2,136
for 7 nights, 1 home
NZ$305 per night
includes taxes & fees
Family Home in the mountains. Get out and explore!
Property grounds
Exterior
Dining
Pool
Very good
(6 reviews)

Crafts Inn, Hotel Suite with pool and hot tub.

Wilmington

8% off
NZ$3,379
for 7 nights, 1 room
NZ$483 per night
includes taxes & fees
Crafts Inn, Hotel Suite with pool and hot tub.
On Site Trails
Interior
Living area
Exterior
Exceptional
(97 reviews)

The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome

Whitingham

11% off
NZ$2,926
for 7 nights, 1 home
NZ$418 per night
includes taxes & fees
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
Private kitchen
Dining
Room
Living area
Exceptional
(5 reviews)

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

West Dover

12% off
NZ$6,647
for 7 nights, 1 home
NZ$950 per night
includes taxes & fees
Riverside Home on Route 100 on Moover Bus Stop-3 Miles From Mount Snow
Room
Living area
Dining
Interior
Exceptional
(5 reviews)

Charming Home with Lake and Mountain View

Whitingham

8% off
NZ$10,976
for 7 nights, 1 cabin
NZ$1,568 per night
includes taxes & fees
Charming Home with Lake and Mountain View
Condo View
Carinthia lodge fire pit
Dining
Living area
Exceptional
(46 reviews)

Ski In/Ski Out at Carinthia Base

West Dover

16% off
NZ$7,534
for 7 nights, 1 apartment
NZ$1,076 per night
includes taxes & fees
Ski In/Ski Out at Carinthia Base
Terrace/patio
Pool
Fitness facility
Games room
Exceptional
(29 reviews)

Ski In/Out at Mt Snow at Seasons w/Fireplace

West Dover

16% off
NZ$6,553
for 7 nights, 1 apartment
NZ$936 per night
includes taxes & fees
Ski In/Out at Mt Snow at Seasons w/Fireplace

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Book a holiday rental for your Whitingham getaway

Enjoy the wineries and other features of Whitingham. One of the city's many top draws is its parks. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Whitingham

Do you want to discover top things to see and do while you're in town? Venture out of your cosy holiday rental and check out everything that Whitingham has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • The Hermitage Golf Club (7.6 mi / 12.2 km)
  • The Hermitage Club (9.3 mi / 15 km)
  • Mount Snow Golf Course (10.3 mi / 16.6 km)
  • Prospect Mountain Cross-Country Ski Center (11.2 mi / 18 km)
  • Berkshire East Ski Resort (11.9 mi / 19.2 km)
  • Mount Snow (11.9 mi / 19.2 km)

Exploring the natural landscape of Whitingham

Whether you're an active traveller or just want to take in the scenery, Whitingham is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Harriman Reservoir (2.8 mi / 4.5 km)
  • Jacksonville Pond (3.5 mi / 5.6 km)
  • Hogback Mountain Conservation Area (6.7 mi / 10.8 km)
  • Lake Raponda (6.8 mi / 11 km)
  • Snow Lake (12.2 mi / 19.6 km)
  • Windsor Lake Park (12.9 mi / 20.8 km)

Transport options to and around Whitingham

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 32.6 mi (52.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Whitingham when booking a holiday rental?
When considering a holiday rental in Whitingham, Vermont, the best area to stay is near the charming village centre. This neighbourhood not only offers a quaint, picturesque setting but also provides easy access to some of the area's top attractions. Just a short drive away, you can explore the stunning Harriman Reservoir, which is superb for outdoor activities such as hiking, fishing, and boating. Additionally, the nearby Green Mountain National Forest is a fantastic spot for those who enjoy nature and scenic views.In terms of accommodations, the village centre has a variety of properties ranging from cosy cabins to spacious holiday homes, ensuring that visitors can find something that suits their needs. Staying in this area allows you to immerse yourself in the local culture while being close to the natural beauty that Vermont is renowned for.
Where are the best Whitingham ski resort rentals?
For the best ski resort rentals near Whitingham, Vermont, travellers should consider the nearby area of Wilmington and the quaint community of Dover. These towns provide convenient access to the nearby Mount Snow ski area, which is renowned for its extensive slopes and varied terrain. In Wilmington, visitors can find charming cabins and lodges that typically feature amenities such as wood-burning fireplaces, spacious living areas, and fully equipped kitchens, making them superb for families or groups seeking a cozy retreat after a day on the mountain.In Dover, there are also a variety of rental options, including modern condos and townhouses that often come with ski-in/ski-out access, ideal for those looking to maximise their time on the slopes. Many of these properties include amenities like hot tubs, communal lounges, and ski storage facilities, providing added convenience and comfort.Additionally, the surrounding area offers numerous opportunities for outdoor activities beyond skiing, such as snowshoeing and cross-country skiing, with trails accessible from many rental locations. The local scene includes charming shops and restaurants, enhancing the overall experience for visitors looking to enjoy the beauty of Vermont's winter landscape.
What is the most popular type of holiday rental accomodation in Whitingham?
In Whitingham, holiday houses are the most popular type of holiday rental, with around 45 options available throughout the area. These holiday homes typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a comfortable stay. Additionally, there are several cottages, cabins, and chalets, which offer a charming and rustic atmosphere, often with outdoor spaces for relaxation and enjoying the natural surroundings. Apartments are also available, providing a more compact option for travellers.
Are there any family house rentals in Whitingham?
In Whitingham, Vermont, there are numerous family-friendly house rentals available—specifically, around 18 options to choose from. The area is known for its scenic beauty and outdoor activities, making it an excellent choice for families seeking adventure and relaxation. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces great for kids to play.Visitors can often find amenities such as Wi-Fi, laundry facilities, and sometimes even game rooms or fireplaces for cosy evenings together. The locale is close to several attractions, including the stunning Mount Snow for skiing in winter and beautiful hiking trails during the warmer months.
Can I rent a holiday home with a pool or hot tub in Whitingham?
In Whitingham, Vermont, there are several holiday homes available for rent that feature pools and hot tubs, making it an appealing destination for those seeking relaxation and leisure. The area is known for its scenic beauty, surrounded by lush green mountains and tranquil lakes. Many of these rentals come with amenities such as private pools, hot tubs, expansive outdoor decks, and fully equipped kitchens, allowing guests to enjoy both indoor and outdoor living.Properties in this region often cater to families or groups, providing spacious living areas and comfortable accommodations. Additionally, the serene environment is superb for unwinding after a day of exploring the local trails or enjoying water activities in the nearby lakes.
Are there pet-friendly house rentals in Whitingham?
In Whitingham, Vermont, there are several pet-friendly house rentals available, with around twelve options for travellers to choose from. Many of these properties offer a variety of amenities, such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.The area is particularly appealing for those seeking a tranquil retreat, as it is surrounded by beautiful natural landscapes. For outdoor enthusiasts, nearby attractions like the Green Mountain National Forest provide ample opportunities for hiking and exploring with pets. The picturesque surroundings make it an excellent choice for travellers looking to enjoy both comfort and nature during their stay.
Are there any remote work holiday rentals in Whitingham?
In Whitingham, Vermont, there are numerous options for remote work holiday rentals, with around 63 available for travellers seeking a conducive environment. Many of these properties come equipped with essential amenities such as complimentary Wi-Fi and comfortable workspaces, allowing guests to stay productive while enjoying the serene surroundings.The area offers a tranquil setting, great for those looking to balance work and relaxation. With access to beautiful natural landscapes, including nearby lakes and hiking trails, guests can take advantage of outdoor recreational activities during their downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Whitingham?
In Whitingham, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing a lovely outdoor space to relax and enjoy the surrounding nature. A fireplace is a common amenity, great for cosy evenings after a day of outdoor activities. Onsite parking is available, making it convenient for those travelling by car. Additionally, many rentals come with coffee and tea makers, ensuring guests can enjoy a warm beverage at any time.
When is the best time to visit Whitingham for a holiday rental?
The best time to visit Whitingham for a holiday rental is during the peak season from June to August, with July being the most popular month. This sunny period attracts travellers seeking outdoor adventures, from hiking and biking to enjoying the serene beauty of the surrounding Green Mountains. With temperatures typically ranging from 15 to 25 degrees Celsius, the weather is superb for exploring Whitingham's picturesque landscapes and indulging in various recreational activities.During these summer months, the town comes alive with tourists taking advantage of the warm weather, making it a vibrant time to experience local events and community gatherings. The inviting atmosphere encourages socialising and discovering the charming local shops and eateries, ideal for those looking to immerse themselves in the local culture.For those considering a more budget-friendly option, November offers a quieter experience. While the summer crowds have dispersed, it's a lovely time to appreciate the tranquil beauty of Whitingham, with the stunning autumn foliage still visible early in the month. Visitors can enjoy peaceful hikes and scenic drives without the hustle and bustle of peak tourist season.Ultimately, the best time to book your holiday rental in Whitingham will depend on your preference for lively summer adventures or the calm beauty of the shoulder months.
What are the top attractions in Whitingham?
In Whitingham, Vermont, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The picturesque Harriman Reservoir is a significant draw, offering opportunities for boating, fishing, and picnicking along its shores. Nearby, the Green Mountain National Forest provides extensive trails for hiking, mountain biking, and stunning scenic views, especially in the autumn when the foliage transforms into a vibrant tapestry of colours.For those interested in winter sports, the area is close to ski resorts like Mount Snow, which is popular for skiing and snowboarding. The charming village of Wilmington, just a short drive away, features quaint shops, local eateries, and the historic Adams Family Farm, where visitors can learn about farming and local produce.
Are all fees included in the Whitingham 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 Whitingham holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Whitingham 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 Whitingham holiday homes?
You can find great discounts on holiday homes in Whitingham 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 Whitingham holiday home booking on Bookabach?
To find Whitingham 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 Whitingham?
A long-stay holiday home in Whitingham 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 Whitingham holiday home?
Book your Whitingham 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 Whitingham?
Prices for holiday homes in Whitingham 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 Whitingham 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.