Winchendon holiday lettings

We found 84 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Winchendon that are perfect for your trip. Holiday rentals provide the amenities that you need and want for your family, friends or furry companion, such as parking and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winchendon

Showing deals for:1 Jan - 8 Jan

Dining
Interior
Living area
Private kitchen
Exceptional
(10 reviews)

Lake House on walking trail, 10 minutes from Mt. Monadnock.

Rindge

8% off
£3,069
for 7 nights, 1 home
£438 per night
includes taxes & fees
Lake House on walking trail, 10 minutes from Mt. Monadnock.
Living room
Dining Room view
Living room
Living room
Exceptional
(83 reviews)

Secluded chalet on 50 acres at base of Mt Monadnock, near lakes -TESLA charger

Jaffrey

8% off
£2,461
for 7 nights, 1 home
£352 per night
includes taxes & fees
Secluded chalet on 50 acres at base of Mt Monadnock, near lakes -TESLA charger
Exterior
Terrace/patio
Property grounds
Interior
Exceptional
(12 reviews)

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

Ashburnham

8% off
£1,885
for 7 nights, 1 home
£269 per night
includes taxes & fees
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!
Dining
Exterior
Exterior
Interior
Exceptional
(5 reviews)

Marians Place Mountain Lake Escape!

New Ipswich

8% off
£2,011
for 7 nights, 1 home
£287 per night
includes taxes & fees
Marians Place Mountain Lake Escape!
Exterior
Property grounds
Interior
Room
Exceptional
(23 reviews)

Quiet private pond getaway

New Ipswich

8% off
£1,444
for 7 nights, 1 home
£206 per night
includes taxes & fees
Quiet private pond getaway
Property grounds
Property grounds
Living area
Room
Exceptional
(5 reviews)

2 Bedroom Spacious Cottage on pond

Hubbardston

8% off
£2,085
for 7 nights, 1 home
£298 per night
includes taxes & fees
2 Bedroom Spacious Cottage on pond

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Choose a holiday rental for your Winchendon getaway

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Winchendon. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Winchendon

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and check out everything that makes Winchendon a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Cathedral of the Pines (6.8 mi / 10.9 km)
  • Shattuck Golf Course (10.2 mi / 16.5 km)
  • 1761 Old Mill Gift Shop (11.4 mi / 18.4 km)
  • Game On Fitchburg (12.6 mi / 20.2 km)
  • Great Wolf Lodge Waterpark (13.6 mi / 21.9 km)
  • Wachusett Mountain Ski Area (15.3 mi / 24.6 km)

Exploring the natural features in Winchendon

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Winchendon is a great place to get outside. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Laurel Lake (6.6 mi / 10.6 km)
  • Contoocook Lake (7.3 mi / 11.7 km)
  • Wapack Trail (13.9 mi / 22.4 km)
  • Miller State Park (14.5 mi / 23.3 km)
  • Pack Monadnock Mountain (14.8 mi / 23.9 km)
  • Swanzey Lake (17.1 mi / 27.6 km)

How to get to and around Winchendon

Fly into Nashua, NH (ASH-Nashua Municipal), the closest airport, located 28 mi (45.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Worcester, MA (ORH-Worcester Regional), which is 30.1 mi (48.5 km) away.

Frequently asked questions

What is the best area to stay in Winchendon when booking a holiday rental?
When considering a holiday rental in Winchendon, Massachusetts, the most appealing area to stay would be near the quaint downtown district. This charming neighbourhood boasts a selection of properties that cater to various tastes and budgets, allowing visitors to immerse themselves in the local culture. One of the highlights of this area is the Winchendon Historical Society, where you can delve into the rich history of the region. Additionally, the nearby Lake Monomonac offers a picturesque setting for outdoor activities such as swimming, fishing, and hiking, making it a great spot for nature enthusiasts.
How much does it cost to rent a holiday home in Winchendon?
Prices for holiday rentals in Winchendon 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 Winchendon 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 Winchendon holiday house rentals?
You can find great discounts on house rentals in Winchendon 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.
What is the most popular type of holiday rental accomodation in Winchendon?
In Winchendon, holiday houses are the most popular type of holiday rental, with around 28 available throughout the area. These residences typically provide spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas ideal for families or groups. Many also include outdoor spaces such as patios or decks, superb for enjoying the scenic views of the surrounding countryside. Additionally, there are about 12 cottages available, which offer a cozier, more intimate setting, often with rustic charm and easy access to local attractions.
Are there any family house rentals in Winchendon?
In Winchendon, Massachusetts, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area offers a variety of spacious properties, often featuring multiple bedrooms, well-equipped kitchens, and inviting living areas for family gatherings. Many homes also include outdoor spaces, ideal for children to play and enjoy the fresh air.Visitors to Winchendon can explore nearby attractions such as Lake Monomonac, which provides opportunities for swimming, fishing, and picnicking. The scenic surroundings make it superb for outdoor activities, including hiking and biking. Families can also discover local parks and recreational areas, ensuring a memorable stay filled with both relaxation and adventure.
Can I rent a holiday home with a pool or hot tub in Winchendon?
In Winchendon, there are several holiday homes available for rent that feature pools and hot tubs, making it a great option for those seeking relaxation and recreation. The area is known for its picturesque landscapes and tranquil environment, ideal for families and groups. Many of these properties come equipped with amenities such as private pools, hot tubs, outdoor seating areas, and fully furnished kitchens, allowing guests to enjoy both indoor and outdoor living.
Can I find long-stay holiday rentals in Winchendon?
A long-stay holiday rental in Winchendon 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Winchendon?
In Winchendon, Massachusetts, there are several pet-friendly house rentals available, making it a great choice for travellers who wish to bring their furry companions along. Many of these properties offer comfortable amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces where pets can enjoy the fresh air.The area is surrounded by beautiful natural scenery, including the nearby Lake Monomonac, which provides opportunities for outdoor activities such as hiking, fishing, and boating. Additionally, the local parks in and around Winchendon offer ample space for walking dogs and enjoying nature.
Are there any remote work holiday rentals in Winchendon?
In Winchendon, Massachusetts, there are several remote work-friendly holiday rentals available, with around 36 properties suiting those needing a productive environment. Many of these rentals provide essential amenities for remote work, including reliable Wi-Fi, designated laptop workspace, and comfortable living areas, ensuring a conducive atmosphere for working from home.The town itself offers a quaint New England charm with access to local parks and natural beauty, great for taking breaks and enjoying the outdoors. Nearby attractions such as Lake Monomonac provide opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winchendon holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Winchendon 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 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 Winchendon?
In Winchendon, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoying the surrounding scenery. Onsite parking is another common amenity, making it convenient for travellers with vehicles. Additionally, rentals often come equipped with essentials like blenders and coffee or tea makers, enhancing the comfort of guests as they unwind in this charming Massachusetts town.
When is the best time to visit Winchendon for a holiday rental?
The peak season for holiday rentals in Winchendon is during the summer months of June to August, with July being the most popular time to visit. This vibrant period attracts families and outdoor enthusiasts who flock to the area to enjoy the warm weather and partake in various recreational activities, such as hiking and fishing in the picturesque surroundings.During these summer months, you can bask in pleasant temperatures ranging from 20 to 30 degrees Celsius, making it an ideal time for exploring local parks and lakes. Winchendon offers stunning outdoor spaces where you can immerse yourself in nature, whether you're picnicking by the water or embarking on scenic trails.If you're looking for a more budget-friendly option, consider visiting in December. While this is the low season, it brings a unique charm to Winchendon, with opportunities for winter activities like snowshoeing and enjoying the holiday decorations around town. The quieter atmosphere allows for a more relaxed exploration of local attractions and cosy moments by the fire.Ultimately, the best time to visit Winchendon for a holiday rental depends on your preferences: whether you wish to embrace the lively summer scene filled with outdoor adventures or enjoy the peacefulness and festive spirit that December brings.
How early should I book a Winchendon holiday rental?
Book your Winchendon holiday 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 holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winchendon?
In Winchendon, visitors can experience a charming small-town atmosphere with several attractions to explore. The Winchendon History and Cultural Centre offers insights into the local heritage and hosts various community events throughout the year. The beautiful Lake Monomonac is a popular spot for outdoor activities such as swimming, fishing, and kayaking, providing a serene setting for nature enthusiasts.For those interested in hiking, the nearby Monadnock State Park offers trails with stunning views and opportunities for wildlife observation. The quaint downtown area features local shops and eateries, making it a pleasant place to stroll and enjoy the community vibe. Additionally, the nearby Gardner Museum showcases art and history, adding to the cultural offerings in the region.
Can I change or cancel my Winchendon home rental booking on Vrbo?
To find Winchendon holiday 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 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 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, Vrbo 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 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 Winchendon holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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