Dover Plains holiday homes

We found 84 holiday rentals — enter your dates for availability
Discover a selection of 5 homes and other holiday rentals in Dover Plains that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, such as air conditioning and Wi-Fi. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

  • 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

Find the perfect holiday rental for your Dover Plains getaway

Learn about the unique charm of Dover Plains 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.

Sightseeing in and around Dover Plains

Do you want to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Dover Plains a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Millbrook Vineyards and Winery (8.9 mi / 14.4 km)
  • Hopkins Vineyard (11.7 mi / 18.9 km)
  • Mohawk Mountain Ski Area (15.2 mi / 24.4 km)
  • Thunder Ridge Ski Resort (16.1 mi / 25.9 km)
  • Trevor Zoo (8.2 mi / 13.2 km)
  • Clinton Vineyards (12.9 mi / 20.8 km)

Exploring the natural landscape of Dover Plains

Whether you're an outdoor enthusiast or just want to take in the scenery, Dover Plains is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Kent Falls State Park (8.5 mi / 13.7 km)
  • Lake Waramaug State Park (10.2 mi / 16.4 km)
  • Lake Waramaug (11.5 mi / 18.5 km)
  • Candlewood Lake (18.2 mi / 29.4 km)
  • Walkway Over the Hudson State Historic Park (19.4 mi / 31.2 km)
  • Innisfree Garden (9.1 mi / 14.6 km)

Travelling to and around Dover Plains

The nearest airport is in Danbury, CT (DXR-Danbury Municipal), located 25.9 mi (41.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Oxford, CT (OXC-Waterbury - Oxford), which is 29 mi (46.7 km) away.

Frequently asked questions

What is the best area to stay in Dover Plains when booking a holiday rental?
When considering a holiday rental in Dover Plains, New York, the area around the town centre is particularly appealing. This charming neighbourhood offers a quaint, small-town atmosphere with a selection of properties that cater to various preferences. You'll find a mix of historic homes and modern accommodations, making it a delightful spot for visitors.Nearby, the scenic Harlem Valley Rail Trail is a top attraction, great for walking, cycling, or simply enjoying the beautiful surroundings. Additionally, the area is close to the picturesque Stissing Mountain, which provides excellent hiking opportunities and stunning views of the surrounding landscape.Staying in this central location allows for easy access to local eateries and shops, providing a true taste of the community.
Where are the best Dover Plains ski resort rentals?
For skiing near Dover Plains, the closest ski resort is in the Catskill Mountains, specifically around areas like Hunter Mountain and Windham Mountain, which are about an hour's drive away. In the vicinity of these resorts, travellers can find a variety of holiday rentals in towns such as Tannersville and Windham.In Tannersville, you can expect to find charming cabins and lodges that cater to winter sports enthusiasts. Many of these properties offer amenities like fully equipped kitchens, spacious living areas with fireplaces, and outdoor decks that provide stunning mountain views. Some rentals even include hot tubs, great for relaxing after a day on the slopes.Windham also presents a selection of rentals, ranging from modern condos to rustic chalets, often featuring amenities such as ski storage, laundry facilities, and access to communal hot tubs or pools. The area is well-serviced, with local shops and dining options that enhance the convenience for guests.For those interested in additional activities, the Catskills offer numerous hiking trails and scenic spots, especially in the spring and summer months.
What is the most popular type of holiday rental accomodation in Dover Plains?
In Dover Plains, both campsites and holiday houses are equally popular, with approximately 12 of each available in the area. These rentals are typically situated in tranquil locations, allowing guests to immerse themselves in the natural beauty of the Hudson Valley. Campsites offer a rustic experience, providing amenities such as fire pits and picnic tables, great for those looking to connect with nature. Meanwhile, holiday houses often feature multiple bedrooms, fully equipped kitchens, and outdoor spaces for barbeques or simply relaxing after a day of exploring local attractions. Additionally, there are several apartments and cabins, which provide a more home-like atmosphere with cosy living areas and convenient amenities.
Are there any family house rentals in Dover Plains?
In Dover Plains, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features spacious properties that often include amenities such as full kitchens, comfortable living rooms, and outdoor spaces for kids to play. Many homes are situated near local attractions, including the scenic landscapes of the Hudson Valley and nearby parks, offering opportunities for hiking and picnicking.Visitors can enjoy easy access to the charming local community, where they can explore quaint shops and eateries.
Can I rent a holiday home with a pool or hot tub in Dover Plains?
In Dover Plains, there are several holiday homes available for rent that feature pools and hot tubs, providing a lovely retreat for travellers seeking relaxation. This charming area in New York offers a mix of scenic beauty and tranquil surroundings, making it an appealing destination for a getaway.Many of these properties come equipped with private swimming pools, hot tubs, and spacious outdoor areas, ideal for enjoying the fresh air and picturesque views. Inside, guests can expect amenities such as fully equipped kitchens, comfortable living spaces, and modern conveniences like Wi-Fi and air conditioning.
Are there pet-friendly house rentals in Dover Plains?
In Dover Plains, there are several pet-friendly house rentals available, making it an excellent destination for travellers with furry companions. Many of these properties feature amenities such as spacious backyards, which are great for pets to roam and play, as well as comfortable living spaces equipped with kitchens for convenient self-catering.The neighbourhood is surrounded by beautiful natural scenery, with opportunities for outdoor activities such as hiking and exploring the nearby scenic trails. Notably, the area is close to the Harlem Valley Rail Trail, which is pet-friendly and offers a lovely setting for walks and bike rides.
Are there any remote work holiday rentals in Dover Plains?
In Dover Plains, New York, there are about 28 remote work-friendly holiday rentals available. This charming town, located in the scenic Hudson Valley, offers a range of accommodations suitable for those looking to combine work and leisure. Many properties provide essential amenities such as complimentary Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas, ensuring a conducive environment for remote work.The area boasts beautiful landscapes, with opportunities for outdoor activities like hiking and visiting local parks. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Dover Plains?
In Dover Plains, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Onsite parking is also a common feature, providing convenience for those travelling by car. Many properties boast decks or patios, superb for enjoying the fresh air and scenic views of the surrounding area. Additionally, rentals often include fireplaces, creating a cosy atmosphere, especially during cooler months. Gardens are another appealing amenity, offering outdoor space for relaxation and enjoyment.
When is the best time to visit Dover Plains for a holiday rental?
The best time to visit Dover Plains, New York, is during the peak season from July to September, with August being particularly popular among travellers. This vibrant period is characterised by warm summer weather, making it ideal for outdoor activities such as hiking and exploring the scenic beauty of the Hudson Valley. Visitors can enjoy the lush landscapes and partake in local events that often take place during these months.August typically welcomes pleasant temperatures, ranging from around 15 to 30 degrees Celsius, providing a comfortable climate for sightseeing and leisurely strolls through charming downtown areas. The vibrant local community comes alive with farmers' markets and seasonal festivals, offering a taste of the region's culture and hospitality.For those looking for a more budget-friendly option, consider planning your visit in December. While this month falls into the low season, it presents a unique opportunity to experience the tranquillity of Dover Plains during the winter months. The serene environment allows for peaceful retreats and opportunities to enjoy winter sports in nearby areas.
What are the top attractions in Dover Plains?
Dover Plains offers a charming selection of attractions that highlight its natural beauty and local history. The area is known for its picturesque landscapes, making it a great spot for outdoor enthusiasts. One of the main attractions is the scenic Appalachian Trail, which runs nearby and provides ample opportunities for hiking and enjoying the stunning views of the Hudson Valley.In the heart of Dover Plains, visitors can explore the quaint downtown area, which features local shops and eateries. The nearby Dover Stone Church is a fascinating natural landmark, where the stunning rock formations create a unique setting for exploration and photography.For those interested in history, the Harlem Valley Rail Trail is a lovely spot to walk or bike while taking in the historical significance of the area. This trail, which was once a railway line, offers a peaceful experience amidst the natural surroundings.
Are all fees included in the Dover Plains 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 Dover Plains holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Dover Plains 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 Dover Plains holiday homes?
You can find great discounts on holiday homes in Dover Plains 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 Dover Plains holiday home booking on Bookabach?
To find Dover Plains 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 Dover Plains?
A long-stay holiday home in Dover Plains 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 Dover Plains holiday home?
Book your Dover Plains 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 Dover Plains?
Prices for holiday homes in Dover Plains 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 Dover Plains 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.