Best Vacation Homes in Portsmouth
1256 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $450/Night
For 7 Nights US $3,148
2497.23 ft²
6 Guests
3 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Pool
- Parking
US $299/Night
For 7 Nights US $2,093
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $618/Night
For 7 Nights US $4,329
1717 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $375/Night
For 7 Nights US $2,624
161.46 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $152/Night
For 7 Nights US $1,065
1200 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $229/Night
For 7 Nights US $1,605
1100 ft²
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $213/Night
For 7 Nights US $1,492
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $261/Night
For 7 Nights US $1,824
Portsmouth Luxury Rentals
6000 ft²
15 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $1,362/Night
For 7 Nights US $9,536
18 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $657/Night
For 7 Nights US $4,600
1259.38 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $606/Night
For 7 Nights US $4,244
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $575/Night
For 7 Nights US $4,026
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $533/Night
For 7 Nights US $3,730
2500 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $520/Night
For 7 Nights US $3,637
US $499/Night
For 7 Nights US $3,493
US $499/Night
For 7 Nights US $3,493
Portsmouth Pet Friendly Vacation Rentals
2900 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $336/Night
For 7 Nights US $2,350
21.53 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Parking
- Air Conditioner
US $101/Night
For 7 Nights US $706
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $82/Night
For 7 Nights US $572
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $250/Night
For 7 Nights US $1,752
2895.49 ft²
8 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $416/Night
For 7 Nights US $2,914
950 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $244/Night
For 7 Nights US $1,709
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $192/Night
For 7 Nights US $1,344
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $164/Night
For 7 Nights US $1,147
Portsmouth Large Vacation Homes
6 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Child Friendly
US $1,324/Night
For 7 Nights US $9,268
8 Guests
5 Bedrooms
3 Bathrooms
House
- Balcony/Terrace
- Parking
- Air Conditioner
US $225/Night
For 7 Nights US $1,575
10 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Spa
- Fireplace/Heating
US $427/Night
For 7 Nights US $2,989
7500 ft²
18 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,230/Night
For 7 Nights US $8,608
1847 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Breakfast
- Kitchen
US $316/Night
For 7 Nights US $2,211
6000 ft²
16 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $713/Night
For 7 Nights US $4,991
6150 ft²
14 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,557/Night
For 7 Nights US $10,899
16 Guests
8 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,170/Night
For 7 Nights US $8,193
Why Choose Rent By Owner for your Portsmouth 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.
Popular Areas for Portsmouth Vacation Rentals
Where are the best neighborhoods to stay in Portsmouth?
When choosing where to stay in Portsmouth, Virginia, exploring the diverse neighborhoods can greatly enhance your visit. Each area offers its own unique charm and atmosphere, providing you with a variety of options for your vacation rental experience. Whether you're seeking vibrant streets close to popular attractions or quiet residential streets for relaxation, Portsmouth’s neighborhoods are well-suited to meet your preferences. Naturally situated along the scenic waterways and historic districts, these locations make it easy to immerse yourself in the local culture while enjoying convenient access to everything the city has to offer.
Churchland
This neighborhood offers convenient access to the region’s amenities and a peaceful atmosphere, making it an ideal choice for your stay in Portsmouth. Here, you can enjoy comfortable vacation rentals that provide both comfort and reliability.
View 63+ Rentals in ChurchlandWestern Branch North
Located near the scenic areas of Chesapeake, Western Branch North provides a tranquil setting with easy access to Portsmouth’s attractions. Choose from dependable vacation rentals here for a seamless and enjoyable visit.
View 72+ Rentals in Western Branch NorthBest Times to Visit Portsmouth
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider visiting during the region's shoulder seasons when the weather is pleasant and popular attractions are less crowded, ensuring an enjoyable and relaxed vacation experience in this destination.
Peak Season Highlights
Late Spring to Early Summer (May - June)
During this time, the area experiences warm weather and longer daylight hours, making it ideal for exploring local attractions and enjoying outdoor activities.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Early Fall (September - October)
As summer crowds diminish, you'll find pleasant temperatures and fewer tourists, providing a more relaxed experience while still enjoying favorable weather.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
Off-Season Highlights
Winter (December - February)
The cooler months bring lower tourist activity, offering a quieter visit at the expense of brisker weather, which is perfect for indoor exploration and cozy stays.
Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F
Late Fall to Early Winter (November - December)
This period sees a drop in visitor numbers, providing a tranquil atmosphere ideal for those seeking solitude or to avoid seasonal crowds.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Portsmouth
How to Book Your Portsmouth 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 Portsmouth
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 seating areas perfect for relaxing or dining al fresco during your stay.
- Take advantage of private or shared patios and decks that offer a scenic view of the surrounding area.
- Make use of well-maintained lawns or gardens ideal for outdoor activities or family gatherings.
- Benefit from access to swimming pools or hot tubs, common amenities in many vacation rentals here.
- Utilize designated BBQ grills for outdoor cooking and entertaining with friends and family.
- Explore nearby walking paths, hiking trails, or biking routes that showcase the region's natural beauty.
- Relax in landscaped courtyards or outdoor fire pits, adding cozy elements to your outdoor experience in this destination.
Top Attractions Around Portsmouth
What attractions are nearby?
While staying here, you can explore nearby parks, historical sites, and waterfront attractions that offer a variety of outdoor activities and cultural experiences in Portsmouth, Virginia.
Family Activities
- Children's Museum of Virginia: Engage your family with interactive exhibits and hands-on activities that make learning fun for all ages in this educational attraction.
- Portsmouth Naval Shipyard Museum: Discover maritime history through fascinating exhibits and guided tours that offer insight into the area's naval heritage and shipbuilding stories.
- Fort Nelson Park: Enjoy outdoor adventures and scenic views at this waterfront park, perfect for picnics, playground visits, and relaxing by the water.
- High Street Craft Beer & Wine: Experience a family-friendly environment with local craft beverages and communal spaces that invite everyone to unwind after exploring the region.
Adult Activities
- Portsmouth Naval Shipyard Museum: Discover the rich maritime history of the region through engaging exhibits and interactive displays that bring Portsmouth's naval heritage to life.
- Harbor Cruises and Water Tours: Enjoy a relaxing water-based activity by exploring the scenic harbor, offering unique views of the area's waterfront and naval facilities.
- Downtown Historic District: Stroll through this charming district to experience the area's vibrant local culture, boutique shopping, and inviting cafes.
- Sailing and Boating Adventures: Take advantage of the area's beautiful waterways by booking a sailing or boating excursion tailored for adults seeking adventure or tranquility on the water.
Other Places to Stay in Portsmouth, VA
Tidewater Yacht Marina
Commodore Theatre
Hill House Museum
Frank D Lawrence Stadium
Virginia Sports Hall of Fame and Museum
Children's Museum of Virginia
United States Lightship Portsmouth
Chespeake Bay Diving
Portsmouth Naval Shipyard Museum
Portsmouth City Park
Portsmouth City County
Churchland
Portsmouth Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local History and Culture: Take the time to visit museums and historical sites to truly immerse yourself in the region's rich heritage during your stay.
- Choose Waterfront Accommodation: Opt for vacation rentals near the waterfront to enjoy scenic views and easy access to the area's popular waterways.
- Plan Outdoor Activities: Make the most of the area's parks and outdoor spaces by scheduling activities like walking, biking, or picnicking to enhance your visit.
- Utilize Local Transportation: Use available transit options or walkable neighborhoods to explore the destination comfortably and avoid parking hassles.
Transportation Options
- Portsmouth Transit System: Local buses offer affordable and convenient transportation throughout the area, making it easy for you to explore the region's attractions.
- Rental Cars: Renting a car provides flexibility and comfort as you navigate Portsmouth and its neighboring sites at your own pace.
- Amtrak Intercity Trains: Amtrak services connect here to major cities along the East Coast, offering a reliable option for traveling longer distances.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available, providing quick and direct transportation within the destination.
Local Customs Options
- Portsmouth Seafood Tradition: Participating in the area's rich seafood customs, you’ll find local events celebrating freshly caught Chesapeake Bay delights.
- Historic Celebrations: Engaging in Portsmouth's well-preserved traditions, such as annual reenactments that honor its maritime history and community heritage.
- Southern Hospitality: Expect warm welcomes and courteous manners that reflect the region’s reputation for friendliness and neighborliness.
- Local Art and Craftsmanship: Appreciating Portsmouth's cultural customs through its vibrant art scenes, where handmade crafts and local galleries thrive.
Portsmouth Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Portsmouth?
There are a lot of options in Portsmouth. If you plan on staying in the Portsmouth area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Portsmouth:
- Hidden Gem A Comfortable 4bedroom home with a fenced-in yard.
- Beautiful, modern furnished 3-bedroom, 2-bathroom cottage near attractions.
- Cornick Corner Near Casino
- 3BR Gem Near Rivers Casino – Comfort & Convenience
- Luxe Lakefront Portsmouth Home Fish, Swim and Play!
- Private 1 Bed Apt - Historic Olde Towne Portsmouth
- Portsmouth 2BR/1BA Getaway
- Charming townhome with prime location, upscale amenities, & personalized service
- Portsmouth Waterfront Home - Patio + River Views
- Charming 2-bedroom house in fabulous Portsmouth with WiFi, AC
2. How many vacation rentals have private pools in Portsmouth?
There are 1 vacation rentals with private pools near Portsmouth. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Portsmouth are best for families?
If you are looking for a family-friendly vacation home in Portsmouth, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Portsmouth:
4. How many Rentbyowner vacation rentals are available in Portsmouth?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 231 in the Portsmouth 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 Portsmouth.
5. What is the cancellation policy for vacation rentals in Portsmouth, Virginia?
Cancellation policies vary depending on the individual property listing. It’s important to review the specific cancellation terms provided in the listing details or contact the host directly to understand your options.
6. How do I confirm my booking for a vacation rental in this area?
Confirmation typically occurs once you complete the reservation process and receive a confirmation message from the host or property owner. Always verify your booking details and contact the host if you have any questions prior to arrival.
7. Are there any requirements or restrictions I should know about when booking here?
Each vacation rental may have its own set of rules regarding age, occupancy limits, or pet policies. To ensure a smooth stay, read the property description thoroughly and reach out to the host if clarification is needed.
8. What amenities can I expect at vacation rentals in this region?
Amenities vary among properties but often include essentials like Wi-Fi, parking, and kitchen facilities. Specific amenities are listed in each property’s description, so review these details before booking.
9. How close are vacation rentals in this destination to local attractions and the waterfront?
Many rentals are conveniently located near popular attractions and scenic areas. Check the property location on the map and inquire with the host about proximity to key points of interest for your visit.
Portsmouth Top Rated Vacation Rentals
3 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Pool
US $187/Night
For 7 Nights US $1,309
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $181/Night
For 7 Nights US $1,264
1100 ft²
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $251/Night
For 7 Nights US $1,755
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Breakfast
US $127/Night
For 7 Nights US $890
301.39 ft²
2 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $193/Night
For 7 Nights US $1,349
1 Bathroom
Couples Retreat
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $79/Night
For 7 Nights US $550
1097.92 ft²
7 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- Pool
- Parking
US $319/Night
For 7 Nights US $2,231
7 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $297/Night
For 7 Nights US $2,077
