Boston holiday homes

We found 134 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Boston that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Boston

Showing deals for:1 Jan - 8 Jan

Living area
S'mores anyone?
Interior
Living area
Exceptional
(28 reviews)

Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse

Etlan

8% off
NZ$6,458
for 7 nights, 1 home
NZ$923 per night
includes taxes & fees
Walk to Old Rag | Hot Tub | Dog-Friendly Farmhouse
Master Bedroom with Full Size Bed
Kitchen and Dining Area
Cottage Side View
Fire Pit and Picnic Table
Wonderful
(113 reviews)

Walk to White Oak Canyon Trail in Shenandoah National Park

Syria

12% off
NZ$1,653
for 7 nights, 1 cabin
NZ$236 per night
includes taxes & fees
Walk to White Oak Canyon Trail in Shenandoah National Park
Property grounds
Barn in Snow
View of deck and Blue Ridge from kitchen and great room
Great Room with a view!
Exceptional
(112 reviews)

Serenity and Adventure on Historic Blue Ridge Farm

Sperryville

8% off
NZ$6,368
for 7 nights, 1 home
NZ$910 per night
includes taxes & fees
Serenity and Adventure on Historic Blue Ridge Farm
Summer garden with historic barn, grainery, and large pond in background
The pond and covered dock
Living area
Living area
Exceptional
(117 reviews)

Serenity and adventure at historic Blue Ridge Farm

Sperryville

8% off
NZ$7,056
for 7 nights, 1 home
NZ$1,008 per night
includes taxes & fees
Serenity and adventure at historic Blue Ridge Farm
Exterior
Relax
Interior
Interior
Exceptional
(17 reviews)

Charming 2-bedroom barn with WiFi, AC in brilliant Etlan, minutes from Old Rag.

Etlan

5% off
NZ$2,406
for 7 nights, 1 home
NZ$344 per night
includes taxes & fees
Charming 2-bedroom barn with WiFi, AC in brilliant Etlan, minutes from Old Rag.
Property grounds
Exterior
Interior
Interior
Exceptional
(50 reviews)

The Historic Poorhouse at Cardinal Springs

Sperryville

8% off
NZ$5,683
for 7 nights, 1 home
NZ$812 per night
includes taxes & fees
The Historic Poorhouse at Cardinal Springs
Bedroom 2, king bed
Living area
Property grounds
Interior
Exceptional
(27 reviews)

Walk to Old Rag | Hot Tub | Mountain Farmhouse

Etlan

8% off
NZ$6,331
for 7 nights, 1 home
NZ$904 per night
includes taxes & fees
Walk to Old Rag | Hot Tub | Mountain Farmhouse
Family Room
Kitchen
Front View
Kitchen
Exceptional
(17 reviews)

Respite from Reality

Madison

8% off
NZ$2,635
for 7 nights, 1 home
NZ$376 per night
includes taxes & fees
Respite from Reality
Dining
Terrace/patio
Interior
Exterior
Exceptional
(8 reviews)

Mid-Century Modern Woodland Retreat with Hot Tub, Cold Water Plunge, & Fire Pit!

Culpeper

8% off
NZ$5,203
for 7 nights, 1 home
NZ$743 per night
includes taxes & fees
Mid-Century Modern Woodland Retreat with Hot Tub, Cold Water Plunge, & Fire Pit!
The kitchen and kitchen table
Pool with Winter cover; Farm Cottage and Aunt Judy's House beyond dependencies
Terrace/patio
Coming in the kitchen door
Exceptional
(72 reviews)

The PERFECT LOCATION FOR MAKING MEMORIES THAT WILL LAST A LIFETIME!!

Culpeper

8% off
NZ$2,325
for 7 nights, 1 cottage
NZ$332 per night
includes taxes & fees
The PERFECT LOCATION FOR MAKING MEMORIES THAT WILL LAST A LIFETIME!!
Cottage: Firepit and Patio
Pool
The Front Door of the Cottage with the Blue Ridge Mtns in the distance.
Hay making season on the farm
Exceptional
(146 reviews)

Farm Living, Creature Comforts, & Centrally Located

Culpeper

8% off
NZ$3,817
for 7 nights, 1 cottage
NZ$545 per night
includes taxes & fees
Farm Living, Creature Comforts, & Centrally Located

  • 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

Travel to luxury Boston

The parks and other outdoor surroundings create an inviting atmosphere in Boston. Travellers appreciate the restaurants in this welcoming city. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Boston

Do you want to discover attractions to see while you're in town? Venture out of your holiday home and experience everything that makes Boston a fun spot to go on holiday. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Little Washington Winery (10.5 mi / 16.8 km)
  • Old House Vineyards (13.8 mi / 22.3 km)
  • Early Mountain Vineyards (16.4 mi / 26.3 km)
  • Yogi Bear's Jellystone Park (16.7 mi / 26.8 km)
  • Wisteria Farm and Vineyard (18.6 mi / 29.9 km)
  • Sharp Rock Vineyards (6.7 mi / 10.8 km)

Exploring the natural landscape of Boston

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Boston is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Shenandoah National Park (16.5 mi / 26.6 km)
  • Old Rag Mountain (9.9 mi / 15.9 km)
  • Mary's Rock Summit Trailhead (13 mi / 21 km)
  • Thorton Gap Entrance Shenandoah (13.1 mi / 21.1 km)
  • Stony Man (13.6 mi / 21.9 km)
  • Rose River Falls (15 mi / 24.1 km)

How to get to and around Boston

The nearest airport is in Charlottesville, VA (CHO-Charlottesville-Albemarle), located 32.6 mi (52.5 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into Washington Dulles International Airport (IAD), which is 46.5 mi (74.9 km) away.

Frequently asked questions

What is the best area to stay in Boston when booking a holiday rental?
When considering a holiday rental in Boston, Virginia, the best area to stay in would be around the charming downtown area. This neighbourhood offers a delightful mix of local shops, cafes, and restaurants, making it a vibrant hub for visitors. The area is known for its quaint, historic architecture, which adds to the overall charm of your stay.One of the top attractions nearby is the scenic hiking trails that wind through the beautiful landscapes of the surrounding Blue Ridge Mountains. These trails not only provide stunning views but also offer a chance to immerse yourself in the natural beauty of the region. Additionally, you can explore local vineyards and enjoy some delightful wine tasting experiences, which are a highlight for many visitors.In terms of accommodation, Boston has a selection of properties that cater to various preferences, from cosy cottages to larger homes suitable for families or groups.
What is the most popular type of holiday rental accomodation in Boston?
In Boston, holiday houses and apartments are the most common types of holiday rentals, with several options available in various neighbourhoods. These rentals typically feature modern amenities such as fully equipped kitchens, spacious living areas, and comfortable bedrooms. Many apartments are located close to attractions like the historic Freedom Trail and Boston Common, making them convenient for exploring the city. Holiday houses, often found in quieter residential areas, provide additional space and outdoor areas, making them ideal for families or groups seeking a more private experience.
Are there any family house rentals in Boston?
In Boston, Virginia, there are several family-friendly house rentals available, making it a delightful destination for groups. The area features charming homes with spacious living areas, great for family gatherings. Many of these properties come equipped with full kitchens, allowing for the convenience of preparing meals together, and outdoor spaces where children can play safely.Visitors will appreciate the proximity to natural attractions such as the scenic views along the Blue Ridge Mountains, which offer opportunities for hiking and outdoor activities. Additionally, the town's rich history and local parks provide engaging options for family outings.
Are there any remote work holiday rentals in Boston?
In Boston, Virginia, there are several holiday rentals that cater to remote workers, providing a conducive environment for productivity. Many of these properties come equipped with essential amenities like free Wi-Fi, dedicated workspaces with desks and chairs, ensuring that guests can comfortably manage their work commitments.The town's serene surroundings and welcoming atmosphere make it an ideal spot for those looking to combine work and leisure. Additionally, visitors can explore nearby attractions such as the beautiful countryside and local parks during their downtime, making it a pleasant destination for remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Boston?
In Boston, popular rental amenities typically include kitchens, which allow guests to prepare their own meals, and decks or patios for enjoying the outdoors. Many rentals also feature coffee and tea makers, ensuring that visitors can start their day with a warm beverage. Dining areas are common, providing spaces for meals and gatherings. Additionally, onsite parking is often available, making it convenient for those travelling by car.
What are the top attractions in Boston?
In Boston, Virginia, visitors can enjoy a variety of attractions that showcase the area's rich history and natural beauty. The Boston Historic District offers a glimpse into the past with its charming architecture and well-preserved buildings, making it superb for leisurely strolls. Nearby, the scenic hiking trails of the Blue Ridge Mountains provide ample opportunities for outdoor enthusiasts to explore the stunning landscapes and enjoy activities such as hiking and birdwatching.The area is also home to the historic Washington and Lee National Forest, where visitors can immerse themselves in nature and discover beautiful vistas. For those interested in local culture, the local community often hosts events and festivals that celebrate the region's heritage.
Are all fees included in the Boston 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 Boston holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Boston 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 Boston holiday homes?
You can find great discounts on holiday homes in Boston 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 Boston holiday home booking on Bookabach?
To find Boston 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 Boston?
A long-stay holiday home in Boston 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 Boston holiday home?
Book your Boston 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 Boston?
Prices for holiday homes in Boston 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 Boston 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.

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