Best Vacation Homes in Boston
1075 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R5,136/Night
For 7 Nights R35,956
2497.23 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R4,838/Night
For 7 Nights R33,860
R5,604/Night
For 7 Nights R39,231
1464 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pool
R4,796/Night
For 7 Nights R33,566
4 Guests
2 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Parking
- Internet
R5,224/Night
For 7 Nights R36,562
1080 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pool
R4,599/Night
For 7 Nights R32,190
2500 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R4,725/Night
For 7 Nights R33,075
6751 ft²
20 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R16,929/Night
For 7 Nights R118,512
Boston Luxury Rentals
30 Guests
8 Bedrooms
9 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
R33,103/Night
For 7 Nights R231,718
6386 ft²
16 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R17,127/Night
For 7 Nights R119,887
5181 ft²
14 Guests
6 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R15,641/Night
For 7 Nights R109,490
4400 ft²
16 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R13,841/Night
For 7 Nights R96,882
3762 ft²
12 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R11,365/Night
For 7 Nights R79,559
4404 ft²
10 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
R10,003/Night
For 7 Nights R70,030
1700 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Kitchen
- Parking
R8,632/Night
For 7 Nights R60,435
2630 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Kitchen
- Parking
R7,759/Night
For 7 Nights R54,311
Boston Pet Friendly Vacation Rentals
1464 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
R5,673/Night
For 7 Nights R39,706
1464 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R6,889/Night
For 7 Nights R48,220
2000 ft²
16 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R3,074/Night
For 7 Nights R21,515
720 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R2,910/Night
For 7 Nights R20,369
1100 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
R2,815/Night
For 7 Nights R19,697
2000 ft²
9 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
R5,172/Night
For 7 Nights R36,202
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R1,779/Night
For 7 Nights R12,444
1650 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R2,382/Night
For 7 Nights R16,668
Boston Large Vacation Homes
3001 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R3,546/Night
For 7 Nights R24,822
13 Guests
4 Bedrooms
3 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
R6,655/Night
For 7 Nights R46,583
1900 ft²
11 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
R4,732/Night
For 7 Nights R33,124
13993 ft²
24 Guests
10 Bedrooms
11 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
R26,508/Night
For 7 Nights R185,561
13 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R4,741/Night
For 7 Nights R33,189
36 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
R15,406/Night
For 7 Nights R107,852
3000 ft²
18 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
R11,040/Night
For 7 Nights R77,283
Why Choose Rent By Owner for your Boston Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Boston
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this region ensures you can enjoy its unique charm and local events, making your stay in Boston, Virginia, a memorable experience for all ages.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy the region's pleasant weather and vibrant atmosphere, making it ideal for exploring local attractions and outdoor activities.
Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
Fall (September to October)
This time of year offers comfortable temperatures and beautiful autumn scenery, perfect for soaking in the area's natural beauty and cultural events.
Average Temperature Daytime: 65-75°F - Nighttime: 50-60°F
Off-Season Highlights
Winter (December to February)
You may experience cooler weather and fewer crowds, providing a more peaceful setting for your stay while still enjoying the regional charm.
Average Temperature Daytime: 40-50°F - Nighttime: 30-40°F
Late Fall to Early Winter (November)
As the region transitions into winter, this period offers quieter accommodations and lower prices, ideal if you prefer a more relaxed visit.
Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F
Weekly Weather Forecast for Boston
How to Book Your Boston Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Boston
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor patio or deck to relax and unwind amidst the fresh air.
- Take advantage of a spacious backyard ideal for outdoor dining or family gatherings.
- Benefit from outdoor grilling facilities to prepare delicious meals during your stay.
- Make use of a community pool or hot tub if available, perfect for added leisure in the region.
- Discover scenic garden areas or landscaped surroundings that enhance your outdoor experience.
- Utilize outdoor recreational amenities like tennis courts or walking trails nearby.
- Experience the convenience of parking spaces or garages with easy access to outdoor spaces here.
Top Attractions Around Boston
What attractions are nearby?
While staying here, you'll find plenty of nearby activities to explore, including charming local parks and cultural attractions that showcase the unique character of Boston, Virginia.
Family Activities
- Boston Children's Museum: Engage your family with interactive exhibits and hands-on activities that make learning fun for children of all ages in this vibrant area.
- Freedom Trail: Discover the rich history of the region as you walk along this historic route, offering family-friendly sights and stories about the area's past.
- Boston Common & Public Garden: Relax and enjoy outdoor adventures in the city's central park, perfect for picnics, playground visits, and scenic boat rides during warmer months.
- New England Aquarium: Explore marine life through engaging displays and an impressive Caribbean coral reef exhibit, ideal for inspiring curiosity in young explorers.
Adult Activities
- Historical Museum Tours: Dive into the region's rich history by exploring renowned museums that showcase Boston, Virginia's unique past and cultural heritage.
- Wine Tastings and Vineyard Visits: Enjoy sophisticated wine experiences at local vineyards that highlight the area's renowned viticulture and scenic landscapes.
- Gourmet Dining Experiences: Savor exquisite cuisine at top-rated restaurants where you can indulge in flavors that reflect the culinary charm of this destination.
- Live Performance Venues: Attend captivating concerts, theater shows, or comedy nights at popular entertainment spots nestled within the region’s vibrant arts scene.
Boston Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Take advantage of community happenings to immerse yourself in the area's culture and meet locals during your stay.
- Plan Your Dining Ahead: Discover nearby eateries and make reservations in advance to enjoy authentic regional cuisine without last-minute hassle.
- Utilize Public Transportation: Use the region's transit options to easily access key attractions and save on parking while exploring the area.
- Visit Hidden Gems: Ask your vacation rental host or explore locally advised spots to experience unique sites beyond the usual tourist routes.
Transportation Options
- Boston Transit Authority (MBTA): This regional transportation system offers convenient subway, bus, and commuter rail services to help you explore the area efficiently.
- Rental Cars: Renting a vehicle provides flexibility and ease of access to all the attractions and outdoor destinations around Boston’s region.
- Bike Rentals: Cycling is an eco-friendly way to discover the local neighborhoods and scenic spots here, with many bike-sharing programs available.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are readily accessible for quick, door-to-door transportation in the area.
Local Customs Options
- Southern Hospitality: You’ll notice the welcoming attitude and politeness that are characteristic of the region's friendly locals.
- Participating in local festivals offers an authentic glimpse into the area's cultural traditions and community spirit.
- Historical Respect: Respect for the region’s rich history is evident, especially when engaging with local landmarks and storytelling.
- Food Etiquette: Enjoying traditional regional cuisine involves embracing shared meals and polite conversation, reflecting the area's hospitality customs.
Frequently Asked Questions About Boston?
1. What are the top vacation rentals in Boston?
There are a lot of options in Boston. If you plan on staying in the Boston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Boston:
- Stunning House with Private Pool and Hot Tub on Rural Estate
- 8-Person House with Private Hot Tub on Spectacular Rural Estate
- The Mill House - Peaceful farmhouse retreat with hot tub, fire pit, & fast Wi-Fi
- Sleeps 4 w/screen porch and private Hot Tub
- Bunkhouse at Spring Haven Farm
- 6-Person House with private hot tub and screen porch
- 2 Bedroom 4 person house with private hot tub on Rural Estate
- Walnut Run Farm
- Kovi Bear Cabin near Shenandoah NP, wineries & restauraunts with Wi-Fi
- Old Rag View Horse Farm with Log Lodge and Treehouse
2. Which vacation homes in Boston are best for families?
If you are looking for a family-friendly vacation home in Boston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Boston:
3. How many Rentbyowner vacation rentals are available in Boston?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 47 in the Boston area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Boston.
4. What is the cancellation policy for my vacation rental booking in Boston, Virginia?
The cancellation policy varies by property. You should review the specific listing details or contact the owner directly to understand the terms and any potential fees associated with cancellations.
5. How do I confirm my reservation and what are the payment options available?
Reservation confirmation and payment methods are detailed on each property listing. It’s recommended to read the listing carefully or reach out to the owner to ensure you understand the process and accepted payment options.
6. Are there any house rules or restrictions I should be aware of during my stay?
Each vacation rental may have its own set of house rules or restrictions. These are usually listed on the property page; if not, contact the owner directly to clarify any guidelines or limitations.
7. What should I do if I encounter an issue during my stay at a vacation rental here?
In case of problems, contact the property owner or manager as soon as possible. Many listings also include support contact information to assist you promptly during your visit.
8. Is there a minimum stay requirement for booking a vacation rental in this destination?
Minimum stay requirements can differ between properties. To find out, review the specific listing details or contact the owner to confirm availability and duration restrictions.
Boston Top Rated Vacation Rentals
9 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
R8,333/Night
For 7 Nights R58,339
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Hot Tub
- Fireplace/Heating
- Pool
R3,766/Night
For 7 Nights R26,361
2300 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
R6,140/Night
For 7 Nights R42,980
12000 ft²
4 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Pool
- Pet Friendly
R15,686/Night
For 7 Nights R109,801
600 ft²
4 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Pool
- Balcony/Terrace
- Kitchen
R2,800/Night
For 7 Nights R19,599
