Best Vacation Homes in Pittsville
Cabin
10.0(215 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
Parking
Balcony/Terrace
View
Kitchen
US $218/Night
7 Nights - US $1,529
House
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
753.47 ft²
- Parking
Air Conditioner
Internet
Pet Friendly
US $550/Night
7 Nights - US $3,850
Cottage
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $453/Night
7 Nights - US $3,171
Cabin
10.0(12 Reviews)
1 Bedroom
1 Bath
4 Guests
560 ft²
Hot Tub- Parking
Ocean View- Balcony/Terrace
US $207/Night
7 Nights - US $1,450
House
10.0(1 Review)
3 Bedrooms
2 Baths
11 Guests
1496.18 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $318/Night
7 Nights - US $2,224
Cabin
9.8(194 Reviews)
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $219/Night
7 Nights - US $1,533
House
9.8(65 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $232/Night
7 Nights - US $1,627
House
9.6(225 Reviews)
2 Bedrooms
1 Bath
4 Guests
650 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $215/Night
7 Nights - US $1,505
Pittsville Luxury Rentals
House
10.0(14 Reviews)
8 Bedrooms
8 Baths
22 Guests
8000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $2,498/Night
7 Nights - US $17,483
House
10.0(14 Reviews)
6 Bedrooms
6 Baths
12 Guests
8500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $2,111/Night
7 Nights - US $14,774
House
10.0(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
2400 ft²
- Hot Tub
- Parking
Spa- Balcony/Terrace
US $2,055/Night
7 Nights - US $14,383
House
9.6(15 Reviews)
6 Bedrooms
4 Baths
16 Guests
4900 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- View
US $1,545/Night
7 Nights - US $10,817
House
10.0(4 Reviews)
5 Bedrooms
4 Baths
10 Guests
4250 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $1,440/Night
7 Nights - US $10,082
House
5 Bedrooms
4 Baths
10 Guests
2400.35 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Air Conditioner
US $1,419/Night
7 Nights - US $9,931
House
9.4(35 Reviews)
6 Bedrooms
3 Baths
12 Guests
2240 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,372/Night
7 Nights - US $9,602
House
9.4(68 Reviews)
7 Bedrooms
6 Baths
12 Guests
8000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,343/Night
7 Nights - US $9,398
Pittsville Pet Friendly Vacation Rentals
House
9.2(40 Reviews)
2 Bedrooms
2 Baths
4 Guests
1400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $663/Night
7 Nights - US $4,641
House
9.5(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2098.96 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
US $611/Night
7 Nights - US $4,277
House
10.0(21 Reviews)
4 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $590/Night
7 Nights - US $4,131
House
4 Bedrooms
3 Baths
8 Guests
5349.66 ft²
Private Pool- Hot Tub
- Parking
Pool
US $1,246/Night
7 Nights - US $8,724
House
10.0(9 Reviews)
4 Bedrooms
4 Baths
8 Guests
2000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,069/Night
7 Nights - US $7,482
House
10.0(7 Reviews)
4 Bedrooms
4 Baths
14 Guests
3000 ft²
- Hot Tub
- Parking
- Spa
- Ocean View
US $977/Night
7 Nights - US $6,839
House
10.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $1,083/Night
7 Nights - US $7,578
House
10.0(1 Review)
4 Bedrooms
2 Baths
6 Guests
2912 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $874/Night
7 Nights - US $6,115
Pittsville Large Vacation Homes
House
10.0(40 Reviews)
5 Bedrooms
4 Baths
10 Guests
4170 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,022/Night
7 Nights - US $7,157
House
6 Bedrooms
3 Baths
12 Guests
2238.89 ft²
Oceanfront- Hot Tub
- Parking
Skiing
US $1,150/Night
7 Nights - US $8,051
House
4 Bedrooms
3 Baths
10 Guests
- Air Conditioner
Child Friendly
Laundry
Security/Safety
US $804/Night
7 Nights - US $5,628
House
10.0(26 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $808/Night
7 Nights - US $5,657
House
10.0(16 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $714/Night
7 Nights - US $5,000
House
9.8(109 Reviews)
5 Bedrooms
3 Baths
6 Guests
2200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $304/Night
7 Nights - US $2,130
House
9.8(16 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $762/Night
7 Nights - US $5,336
House
9.8(12 Reviews)
5 Bedrooms
3 Baths
10 Guests
3185 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $997/Night
7 Nights - US $6,982
Why Choose Rent By Owner for your Pittsville 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 Pittsville
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, allowing you to enjoy the best of what this destination has to offer based on seasonal weather patterns and local events.
Peak Season Highlights
Spring (March to May)
During spring, the area experiences mild temperatures and blooming landscapes, making it an ideal time to enjoy outdoor activities and explore scenic surroundings.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Fall (September to November)
Fall offers crisp air and vibrant foliage, creating a picturesque setting perfect for sightseeing and relaxing in your vacation rental.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Summer (June to August)
In summer, the warmer weather encourages outdoor adventures, although it can be busier with visitors seeking recreational activities in this region.
Average Temperature Daytime: 80-90°F - Nighttime: 60-70°F
Winter (December to February)
During winter, cooler temperatures provide a quieter atmosphere, making it a peaceful time to visit if you prefer fewer crowds and cozy accommodations.
Average Temperature Daytime: 40-50°F - Nighttime: 25-35°F
Weekly Weather Forecast for Pittsville
How to Book Your Pittsville 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.
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 outdoor dining with a fully equipped patio or picnic area, perfect for relaxing in the fresh air.
- Take advantage of spacious yards or gardens to unwind or play outdoor games during your stay.
- Make the most of private balconies or decks offering scenic views of the surrounding region.
- Relax by a cozy outdoor fire pit, ideal for evening gatherings and enjoying the cool regional evenings.
- Access to a swimming pool, providing a refreshing escape during warm days in this destination.
- Utilize designated grilling stations or barbecue areas to prepare meals al fresco.
- Explore nearby nature trails or paths directly from your rental, allowing for easy outdoor adventures in the area.
Top Attractions Around Pittsville
What attractions are nearby?
Here, you can explore a variety of outdoor activities and scenic attractions that showcase the natural beauty of the region surrounding your vacation rental in Pittsville, Virginia.
Family Activities
- Explore the Pocomoke River State Park: You can enjoy hiking, fishing, and picnicking in this scenic park nestled near Pittsville, offering outdoor adventures for the whole family.
- Visit the Benjamin Banneker Historical Park and Museum: Dive into local history and learn about the region’s heritage through engaging exhibits suited for all ages.
- Discover the Assateague Island National Seashore: Experience pristine beaches and observe wild horses, making it a perfect spot for family beach days and nature walks.
- Enjoy a day at the Mar-Va Theater Museum: Immerse yourself in the area's cultural history by exploring historic cinema memorabilia right nearby.
Adult Activities
- Virginia Museum of Fine Arts Tour: You can explore a diverse collection of artwork and cultural exhibits in nearby Richmond, enriching your stay in the region.
- Wine Tasting at Local Vineyards: Indulge in wine tasting experiences at the area’s renowned vineyards, perfect for relaxing outings amidst scenic vineyard views.
- Ornamental Gardens Walks: Enjoy peaceful strolls through beautifully maintained gardens and parks that highlight the natural beauty of this destination.
- Cultural Festivals and Events: Participate in seasonal festivals and community events that showcase the vibrant local culture of this part of Virginia.
Other Places to Stay in Pittsville, VA
Leesville Lake
Pittsville Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead: Research local amenities and attractions in the region to maximize your time and enhance your stay in this charming destination.
- Choose the Right Accommodation: Select a vacation rental that suits your needs and offers easy access to key sites and activities around Pittsville.
- Explore Local Cuisine: Take advantage of the area's culinary offerings by visiting nearby restaurants or preparing homemade meals in your rental’s well-equipped kitchen.
- Respect Community Guidelines: Be mindful of local customs and house rules to ensure a smooth and enjoyable experience for everyone during your visit here.
Transportation Options
- Virginia Railway Express (VRE): This commuter train service connects the area to nearby cities, offering a convenient and scenic transportation option for exploring the region.
- Local Bus Services: Local bus options provide affordable and accessible transportation around Pittsville, making it easy to reach local attractions and amenities.
- Rental Cars: Renting a car here offers flexibility and ease of exploring surrounding areas at your own pace, ideal for accessing remote or less connected destinations.
- Taxis and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available for quick, reliable transit within this destination and nearby locations.
Local Customs Options
- Southern Hospitality: Visitors often experience the warm and welcoming attitude that exemplifies the region's friendly local customs.
- Community Events: Participating in neighborhood gatherings and festivals is a common way to embrace the area's cultural traditions.
- Local Cuisine: Tasting traditional dishes prepared with regional ingredients offers a delicious insight into the area's culinary customs.
- Respect for Nature: Conservation and outdoor etiquette are highly valued here, reflecting the community’s deep connection to its natural surroundings.
Pittsville Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Pittsville?
There are a lot of options in Pittsville. If you plan on staying in the Pittsville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pittsville:
- Cabin 2 at Cedar Key - Serene waterfront setting/No wake cove/Dog friendly!
- Mountain View, waterfront, large quiet cove, gentle lot, covered dock & deep H2O
- Deep Water/Mountain View Waterfront/3 King Beds/Kayaks, SUP
- Beautiful lakeside family or corporate retreat with pool, hot tub, and more!
- Dock w/Boat Slip: Cozy Cabin Near Leesville Lake!
- Cozy house in private Leesville Lake community
- Tradewind Terrace-Mtn View, Kayaks, Paddleboards, Outdoor Kitchen, Generator etc
- Beautiful waterfront lodge, private dock and breath taking views of Smith Mt.
- Come hideaway at the the Blue Heron Hideaway with beautiful wide lake views.
- The Grandview Lodge, Oasis at Smith Mountain Lake!
2. Which vacation homes in Pittsville are best for families?
If you are looking for a family-friendly vacation home in Pittsville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Pittsville:
3. How many Rentbyowner vacation rentals are available in Pittsville?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 146 in the Pittsville 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 Pittsville.
4. What is the cancellation policy for booking a vacation rental here?
Cancellation policies vary depending on the property listing, so it’s important to review the specific terms outlined in the rental agreement. You can usually find this information on the property’s detail page or by contacting the owner directly.
5. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning fees, service charges, or security deposits are often included in the listing details. Be sure to read the full description or contact the host for clarification before completing your booking.
6. How do I know if my reservation will be confirmed instantly or require approval?
Some properties offer instant confirmation, while others may require the owner’s approval. Check the listing details for confirmation type, and reach out to the host if you need further clarification.
7. What amenities are typically available in vacation rentals around here?
Amenities vary by property but commonly include essentials like Wi-Fi, appliances, and outdoor spaces. For specific amenities, review the property listing carefully or contact the owner directly.
8. What should I do if I need to change or cancel my booking during my stay?
Any modifications or cancellations must follow the policies specified in your reservation. Contact the property owner or support team through the booking platform to discuss options and ensure your requests are handled properly.
Pittsville Top Rated Vacation Rentals
House
10.0(56 Reviews)
4 Bedrooms
3 Baths
8 Guests
3600 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $930/Night
7 Nights - US $6,509
Cabin
10.0(38 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $449/Night
7 Nights - US $3,144
House
9.8(23 Reviews)
4 Bedrooms
4 Baths
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,081/Night
7 Nights - US $7,568
House
9.6(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $413/Night
7 Nights - US $2,889
House
8.0(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1350 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $421/Night
7 Nights - US $2,946
House
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
1647 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $335/Night
7 Nights - US $2,346
House
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
US $365/Night
7 Nights - US $2,555
