Whitingham vacation rentals

We found 664 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in Whitingham that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the amenities you need and want, such as WiFi and cable TV. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Whitingham

Showing deals for:Sep 4 - Sep 11

Image gallery for Private 6 bedroom Chalet 5min to Mt Snow

Large living room with endless natural light
9.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Private 6 bedroom Chalet 5min to Mt Snow

West Dover

9% off
Price is $1,236
$8,651 for 7 nights
All fees included
Private 6 bedroom Chalet 5min to Mt Snow

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Find out more about Whitingham

Why visit Whitingham

  1. Outdoor Adventures: Enjoy a range of activities like skiing, hiking, and water sports in the stunning natural surroundings.
  2. Lake Whitingham: Relax or engage in recreational activities at this beautiful lake, perfect for swimming and fishing.
  3. Whitingham Village: Explore the charming village filled with local shops and friendly locals, ideal for a leisurely stroll.
  4. Nearby Parks: Discover the beauty of nearby national and state parks, offering trails and scenic views.
  5. Family-Friendly Fun: Experience various family-oriented activities that cater to all ages and interests.

Top attractions near Whitingham

Whitingham, Vermont, is a fantastic destination for outdoor and adventure enthusiasts, offering a variety of attractions such as Lake Whitingham, Whitingham Village, and nearby national and state parks. Visitors can enjoy nature reserves, cultural experiences, and family-friendly activities, making it perfect for all kinds of travelers. Whether you're exploring the lake or the charming village, Whitingham promises a memorable getaway filled with natural beauty and recreational opportunities.

  1. Jacksonville Pond: Located 3 miles from Whitingham, this picturesque lake offers serene beach vibes, perfect for romantic picnics and outdoor activities surrounded by beautiful scenery.
  2. Molly Stark State Park: Situated 6 miles away, this state park is an adventure lover's paradise, featuring stunning landscapes and numerous trails for hiking and exploring the great outdoors.
  3. The Ledge: Just 3 miles from Whitingham, this unique nudist beach provides a liberating experience, allowing visitors to connect with nature in a relaxed, clothing-optional environment.

Things to do recommended for couples

For a romantic getaway in Whitingham, explore the slopes at Mount Snow or Berkshire East Ski Resort, both 12 miles away. For a more intimate experience, visit Honora Winery, just 5 miles away, where you can enjoy wine tasting in a cozy setting.

Things to do recommended for families

Your family will love the wellness vibes at Windsor Lake Park, the adventurous fun at Shelburne Falls Bowling Alley, and the entertaining experiences at Hopkins Observatory, all within a short drive from Whitingham, Vermont. These activities promise memorable moments for all ages!

What do I need to keep in mind when booking a vacation in Whitingham

If you're traveling with a group, bringing your family, accommodating pets, or planning for an extended stay, be sure to prioritize your search filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Whitingham with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Whitingham with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Whitingham: For many families, a trip isn’t truly complete without their furry companion. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Whitingham: If you're seeking vacation rentals with special offers for extended stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Whitingham

Whitingham, Vermont, offers an unforgettable vacation for adventure seekers and outdoor enthusiasts. Nestled among beautiful lakes and open waters, this charming city is perfect for skiing, hiking, and family-friendly excursions. Just a short drive away, downtown Wilmington provides a vibrant atmosphere filled with art and friendly locals. Explore the numerous lakes and immerse yourself in the stunning natural beauty that surrounds this picturesque region.

  • West Dover: Located 10 miles from Whitingham, West Dover is a fantastic destination for skiing and outdoor adventures. This charming city is home to popular ski resorts that attract winter sports enthusiasts from all over. The breathtaking landscapes feature stunning mountains, tranquil lakes, and picturesque valleys, making it perfect for year-round exploration. Whether you're hitting the slopes in winter or hiking the scenic trails in summer, West Dover offers a vibrant outdoor experience that caters to all adventure seekers.
  • Wilmington: Just 6 miles away from Whitingham, Wilmington is another excellent spot for outdoor lovers, particularly those looking to ski and enjoy adventure sports. This quaint city is surrounded by beautiful mountains and lakes, which serve as a backdrop for various outdoor activities. With its proximity to ski fields and resorts, Wilmington provides ample opportunities for skiing and snowboarding in the winter, while the summer months offer a chance to explore the lush landscapes and partake in water activities. Its welcoming atmosphere and charming downtown area make it a great place to unwind after a day of adventure.
  • North Adams: Situated 13 miles from Whitingham, North Adams is known for its rich cultural scene and outdoor activities. This vibrant city is home to an impressive art museum and various public art installations, making it a hub for creativity and inspiration. North Adams also offers access to ski resorts and outdoor adventures, ensuring there's something for everyone. Whether you're keen on exploring the local art scene or hitting the slopes, North Adams provides a unique blend of culture and adventure in a stunning natural setting.

Best time to go to Whitingham

If you're planning a trip to Whitingham, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancy
January19.9°F (-6.7°C)Light RainMostly CloudyAverage
February22.3°F (-5.4°C)Light RainMostly CloudyAverage
March29.8°F (-1.2°C)Light RainMostly CloudyAverage
April41.7°F (5.4°C)Light RainMostly CloudyAverage
May54.3°F (12.4°C)Light RainMostly CloudyAverage
June61.9°F (16.6°C)Light RainMostly SunnySlightly High
July67.8°F (19.9°C)Light RainMostly SunnySlightly High
August65.8°F (18.8°C)Light RainMostly SunnySlightly High
September59.2°F (15.1°C)Light RainMostly SunnyAverage
October47.8°F (8.8°C)Light RainMostly CloudySlightly Low
November35.8°F (2.1°C)Light RainMostly SunnySlightly Low
December26.6°F (-3.0°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming travels? Being flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilize our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers an easy and organized way to plan your travels. You can create new trips, continue from where you last stopped, or review your existing plans all in one place. Your saved or booked properties will be neatly categorized under Potential, Upcoming, or Current Trips for your convenience. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

Book a vacation 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 accommodations with space to entertain friends and family, Vrbo 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

Are you searching for attractions to visit while you're in town? Venture out of your cozy vacation rental and check out everything that makes Whitingham a fun spot to vacation. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Prospect Mountain Nordic Ski Center (11.7 mi / 18.8 km)
  • Berkshire East Ski Resort (11.9 mi / 19.2 km)

Exploring the natural landscape of Whitingham

Whether you're an outdoor enthusiast or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Whitingham. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city center:

  • 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)
  • North Branch Deerfield River (8.9 mi / 14.4 km)
  • Campers Beach (12.7 mi / 20.4 km)

Transportation 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 center.

Frequently asked questions

How much does it cost to rent a vacation home in Whitingham?
Prices for vacation rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Whitingham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Whitingham vacation house rentals?
You can find great discounts on house rentals in Whitingham on Vrbo, 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.
Where are the best Whitingham ski resort rentals?
For the best ski resort rentals near Whitingham, Vermont, travelers should consider the nearby area of Wilmington, which is just a short drive from the Mount Snow ski resort. This picturesque town offers a variety of accommodations, including cozy cabins and spacious chalets that cater to different group sizes. Many of these properties come equipped with amenities such as wood-burning stoves, hot tubs, and large outdoor decks, great for relaxing after a day on the slopes.

In the Wilmington area, you can find vacation rentals that offer easy access to local dining options and shops, enhancing the convenience for visitors. Some properties may also feature ski storage facilities, allowing guests to store their gear securely.

For those looking for a more rustic experience, the surrounding woods provide opportunities for cross-country skiing and snowshoeing, with trails starting right from some of the rental homes. This region not only provides access to skiing but also showcases the beautiful Vermont landscape, making it a charming choice for winter getaways.
What is the most popular type of vacation rental accomodation in Whitingham?
In Whitingham, vacation houses are the most prevalent type of rental, with about 15 available throughout the area. These homes provide ample space and comfort, typically featuring multiple bedrooms, fully equipped kitchens, and cozy living areas for relaxation after a day of exploring. In addition to vacation houses, several cottages, cabins, and chalets can also be found, offering unique and charming stays that blend seamlessly with the natural surroundings. These properties often include outdoor spaces for enjoying the picturesque Vermont landscape.
Are there any family house rentals in Whitingham?
In Whitingham, Vermont, there are numerous family-friendly house rentals available—about 18 in total. This charming area is known for its picturesque landscapes and outdoor activities that cater to all ages. Many properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and cozy dining spaces great for gatherings.

Visitors can also find homes with amenities such as game rooms for entertainment, outdoor decks for enjoying the fresh air, and even access to private yards where children can play safely.

Located near the scenic Harriman Reservoir and surrounded by the Green Mountain National Forest, families can easily engage in hiking, fishing, and boating activities.
Can I rent a vacation home with a pool or hot tub in Whitingham?
In Whitingham, Vermont, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for travelers seeking relaxation and recreation. The area is known for its picturesque landscapes and proximity to outdoor activities, providing a serene backdrop for a getaway.

Many of these rentals come equipped with amenities such as private pools, hot tubs, spacious living areas, and fully stocked kitchens, ideal for families or groups looking to enjoy quality time together. Additionally, some properties may offer outdoor spaces for barbecuing or lounging, enhancing the overall experience.
Can I find long-stay vacation rentals in Whitingham?
A long-stay vacation rental in Whitingham is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Whitingham?
In Whitingham, there are several pet-friendly house rentals available, providing options for travelers looking to bring their furry companions along. Many of these properties come with amenities such as spacious backyards, outdoor decks, and fully equipped kitchens, great for families or groups seeking a comfortable stay.

The area is known for its picturesque landscapes, including nearby Harriman Reservoir, which offers opportunities for hiking, fishing, and enjoying nature with pets. Additionally, the surrounding Green Mountain National Forest features numerous trails suitable for both human and canine explorers, making it an excellent destination for outdoor enthusiasts.
Are there any remote work vacation rentals in Whitingham?
In Whitingham, Vermont, there are numerous vacation rentals suitable for remote work, with around 21 options available. These properties often provide essential amenities such as high-speed internet and Wi-Fi, ensuring a reliable connection for work-related tasks. Additionally, many rentals feature dedicated workspace areas, allowing travelers to comfortably set up their remote office.

Whitingham is located in a picturesque area, surrounded by nature and offering a serene environment, which can enhance productivity. Visitors can enjoy the local charm and explore nearby attractions such as the Green Mountain National Forest, which offers hiking trails and beautiful scenery for breaks from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Whitingham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Whitingham with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo 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.
What are popular rental amenities in Whitingham?
In Whitingham, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals during their stay. Many rentals feature welcoming decks or patios, ideal for enjoying the serene surroundings and fresh air. Cozy fireplaces are common, providing a warm atmosphere, particularly during the colder months. Onsite parking is typically available, making it convenient for guests with their own vehicles. Additionally, most rentals come with coffee and tea makers, superb for starting the day with a hot beverage.
When is the best time to visit Whitingham for a vacation rental?
The best time to visit Whitingham for a vacation rental is during the peak season from June to August, particularly in July when the area comes alive with vibrant summer activities. This period attracts travelers seeking outdoor adventures, as warm temperatures ranging from the mid-60s to mid-80s Fahrenheit create ideal conditions for hiking, fishing, and exploring the beautiful landscapes that Vermont is famous for.

With plenty of nearby attractions, you'll find opportunities for kayaking on local lakes, biking along scenic trails, and indulging in the charm of the town's quaint shops and restaurants. The lively option during these summer months ensures that you'll be surrounded by fellow adventurers, all eager to enjoy what Whitingham has to offer.

If you're looking for a more budget-friendly option, consider planning your visit in November. This month provides a quieter experience, ideal for those who appreciate the serene beauty of Vermont's fall landscape without the crowds. The crisp air and stunning autumn colors make for picturesque hikes and scenic drives.
How early should I book a Whitingham vacation rental?
Book your Whitingham vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Whitingham, Vermont, United States of America?
In Whitingham, Vermont, visitors can enjoy a variety of attractions that showcase the area's natural beauty and charm. The picturesque Harriman Reservoir is a popular destination for outdoor activities such as kayaking, fishing, and hiking, with scenic views that attract nature lovers year-round. The nearby Green Mountain National Forest offers extensive trails for hiking and mountain biking, providing a superb backdrop for exploring Vermont's stunning landscapes.

The historic town center features quaint shops and local eateries that reflect the region's character and hospitality, making it a pleasant area to stroll and enjoy local cuisine. Additionally, the nearby Vermont Country Store in Weston is a beloved attraction, offering a glimpse into Vermont's rich heritage with a selection of local products and nostalgic goods. For those interested in winter sports, the surrounding areas present opportunities for skiing and snowboarding, with several resorts just a short drive away.
Can I change or cancel my Whitingham home rental booking on Vrbo?
To find Whitingham vacation rentals with free cancellation, just use Vrbo'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". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Whitingham vacation rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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