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Jolliff Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Jolliff vacation rentals

A modern courtyard with white furniture, a central seating area, and a small lawn.

1. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (103 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
$119 nightly
The price is $137
Sep 1 - Sep 2
Total with taxes and fees
stayAPT Suites Suffolk-Chesapeake
A living room with a sectional sofa, a round ottoman, a globe on a shelf, and artwork on the walls.

2. Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.2 out of 10, Wonderful, (26 reviews)
"Great small home would rent again"
United States
Ronnie B.
$294 nightly
The price is $341
Aug 30 - Aug 31
Total with taxes and fees
Comfortable & Private 2 Bedrm Cottage w/ King bed.
A dining room with a round table, four upholstered chairs, a chandelier, and a window with blinds.

3. Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
Portsmouth
9.8 out of 10, Exceptional, (9 reviews)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
$229 nightly
The price is $266
Aug 31 - Sep 1
Total with taxes and fees
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

4. Guesthouse in ideal location with private entrance

Guesthouse in ideal location with private entrance
Suffolk
10.0 out of 10, Exceptional, (6 reviews)
"The property was clean, quiet and had everything we needed for a few days in town to see our grandbabies and daughter. Easy to find, park and just a few blocks from the highway, many food options and Kroger."
United States
Audrey J.
$256 nightly
The price is $293
Sep 6 - Sep 7
Total with taxes and fees
Guesthouse in ideal location with private entrance
A kitchen with granite countertops, stainless steel appliances, and black bar stools.

5. Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
Portsmouth
9.2 out of 10, Wonderful, (30 reviews)
"Pretty clean, convenient location to my daily travel, host was wonderful and very helpful when I needed help with something in the house. I would definitely stay here again."
United States
Niya w.
$271 nightly
The price is $315
Sep 1 - Sep 2
Total with taxes and fees
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
A narrow brick pathway flanked by two houses with siding.

6. Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
Portsmouth
10.0 out of 10, Exceptional, (11 reviews)
"What an awesome place! A perfect location. Close to tons of activities. We would definitely stay again. "
United States
bethany h.
$159 nightly
The price is $186
Aug 30 - Aug 31
Total with taxes and fees
Private 1 Bed Apt - Historic Olde Towne Portsmouth
A living room with a beige sofa, a white ottoman, a patterned rug, a wooden chair, and a small table.

7. Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
Portsmouth
8.6 out of 10, Excellent, (11 reviews)
"It was perfect! Just what we needed for a quick visit with family and could bring the dog!"
United States
Kimberly
$191 nightly
The price is $223
Sep 8 - Sep 9
Total with taxes and fees
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth
A dining area with a wooden table and chairs, a large potted plant, and a white fireplace in the background.

8. Wooded Wonderland

Wooded Wonderland
Portsmouth
9.6 out of 10, Exceptional, (15 reviews)
"Little too cold for swimming but the pool was beautiful. House was very clean and comfortable. We had 8 staying and we didn’t feel on top of each other. One of our party left her jewelry behind but the owner was great and arrangements where made to get them back to her. Would definitely stay again!"
United States
Dawn J.
$563 nightly
The price is $650
Sep 7 - Sep 8
Total with taxes and fees
Wooded Wonderland
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

9. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
10.0 out of 10, Exceptional, (7 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
$111 nightly
The price is $129
Sep 27 - Sep 28
Total with taxes and fees
stayAPT Suites Hampton
A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

10. Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
Portsmouth
9.0 out of 10, Wonderful, (53 reviews)
"Comfortable home and clean quiet stay. "
United States
Lisa H.
$240 nightly
The price is $279
Sep 2 - Sep 3
Total with taxes and fees
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

11. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
$536 nightly
The price is $619
Sep 1 - Sep 2
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

12. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
Portsmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very nice! And the host was in full contact with us throughout our stay to make sure we had everything we needed. Also, our family LOVED the video games. "
United States
Elaine P.
$549 nightly
The price is $634
Sep 1 - Sep 2
Total with taxes and fees
Centrally Located Hampton Roads Home w/ Game Room!
A modern living room with a large window, a flat-screen TV, a white desk, and a blue sofa.

13. The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
$233 nightly
The price is $269
Aug 30 - Aug 31
Total with taxes and fees
The Speakeasy Downtown Newport News
A modern kitchen with white cabinets, stainless steel appliances, and a tiled backsplash.

14. Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
Portsmouth
8.2 out of 10, Very Good, (44 reviews)
"Nice property. Neighborhood was very nice."
United States
John B.
$302 nightly
The price is $350
Sep 1 - Sep 2
Total with taxes and fees
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home
A modern interior with a staircase, a door with a decorative glass panel, and a hallway with a tiled floor.

15. Bright 3-bedroom beach house with AC in charming Norfolk

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.2 out of 10, Wonderful, (7 reviews)
$324 nightly
The price is $380
Aug 31 - Sep 1
Total with taxes and fees
Bright 3-bedroom beach house with AC in charming Norfolk
A living room with a sofa, armchair, glass coffee table, fireplace, and a television.

16. Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
$393 nightly
The price is $393
Aug 31 - Sep 1
Total with taxes and fees
Nyakio Suite - Chesapeake
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

17. Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
$156 nightly
The price is $179
Sep 6 - Sep 7
Total with taxes and fees
Great Studio | Pool & Hot Tub. Your Next Vacation
A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

18. King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
$166 nightly
The price is $191
Sep 6 - Sep 7
Total with taxes and fees
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

19. Cozy 1-bedroom barn in marvelous Hampton with AC

Cozy 1-bedroom barn in marvelous Hampton with AC
Hampton
$179 nightly
The price is $208
Sep 3 - Sep 4
Total with taxes and fees
Cozy 1-bedroom barn in marvelous Hampton with AC
A modern dining area with a glass table, blue upholstered chair, and black chairs.

20. Sojourn | Coastal Cottage | 3 BR

Sojourn | Coastal Cottage | 3 BR
Willoughby Spit
9.4 out of 10, Exceptional, (36 reviews)
"Great little house beach was good for small kids first trip to beach"
United States
Layton H.
$375 nightly
The price is $408
Sep 8 - Sep 9
Total with taxes and fees
Sojourn | Coastal Cottage | 3 BR
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Jolliff Hotel Reviews

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

8/10 Good
"Parking easy Staff nice Room decently clean AC did not work well - room stayed warm which made it difficult to get a good nights sleep"
Cynthia 1-night trip
Posted 2 hours ago
Comfort Suites Chesapeake - Norfolk

Find out more about Jolliff

Everything you need to know about Jolliff vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jolliff vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jolliff vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jolliff vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jolliff. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Jolliff in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $137 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jolliff rentals

At Expedia, we put the best Jolliff vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Jolliff rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jolliff vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jolliff. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Jolliff?

Yes, you can find vacation rentals near popular attractions in Jolliff, or you can go with a more remote option if you want a relaxing place to stay. Jolliff is known for its restaurants and beaches. Make sure you have time to check out the shopping while you're in the area.

What are some of the best vacation home rentals in Jolliff?

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home: This vacation home rental outside of Jolliff is located in the city center and offers a selection of games, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Jolliff?

Explore the area and family-friendly sights such as Children's Museum of Virginia, or get out into nature at a spot like Town Point Park. In the larger area, you’ll find Naval Station Norfolk and Chesapeake Square Mall.

What’s a vacation rental in Jolliff like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Jolliff. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for families.