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Jolliff Vacation Rentals

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Our top choices for Jolliff vacation rentals

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
The price is CA $165
CA $189 total
includes taxes & fees
Sep 1 - Sep 2
stayAPT Suites Suffolk-Chesapeake

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.
The price is CA $162
CA $471 total
includes taxes & fees
Aug 30 - Aug 31
Comfortable & Private 2 Bedrm Cottage w/ King bed.

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.
The price is CA $111
CA $366 total
includes taxes & fees
Aug 31 - Sep 1
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

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.
The price is CA $166
CA $404 total
includes taxes & fees
Sep 6 - Sep 7
Guesthouse in ideal location with private entrance

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)
The price is CA $165
CA $436 total
includes taxes & fees
Sep 7 - Sep 8
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!

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)
The price is CA $112
CA $257 total
includes taxes & fees
Aug 30 - Aug 31
Private 1 Bed Apt - Historic Olde Towne Portsmouth

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)
The price is CA $178
CA $306 total
includes taxes & fees
Sep 16 - Sep 17
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

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.
The price is CA $430
CA $934 total
includes taxes & fees
Sep 7 - Sep 8
Wooded Wonderland

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
The price is CA $157
CA $184 total
includes taxes & fees
Sep 28 - Sep 29
stayAPT Suites Hampton

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.
The price is CA $173
CA $383 total
includes taxes & fees
Sep 2 - Sep 3
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

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

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is CA $403
CA $857 total
includes taxes & fees
Sep 1 - Sep 2
Centrally Located Hampton Roads Home w/ Game Room!

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.
The price is CA $327
CA $874 total
includes taxes & fees
Sep 1 - Sep 2
Centrally Located Hampton Roads Home w/ Game Room!

13. The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is CA $176
CA $386 total
includes taxes & fees
Aug 30 - Aug 31
The Speakeasy Downtown Newport News

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.
The price is CA $179
CA $484 total
includes taxes & fees
Sep 1 - Sep 2
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

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

Bright 3-bedroom beach house with AC in charming Norfolk
Willoughby Spit
9.4 out of 10, Exceptional, (8 reviews)
The price is CA $175
CA $507 total
includes taxes & fees
Aug 31 - Sep 1
Bright 3-bedroom beach house with AC in charming Norfolk

16. Nyakio Suite - Chesapeake

Nyakio Suite - Chesapeake
Greenbrier
The price is CA $278
CA $544 total
includes taxes & fees
Aug 31 - Sep 1
Nyakio Suite - Chesapeake

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.
The price is CA $188
CA $248 total
includes taxes & fees
Sep 6 - Sep 7
Great Studio | Pool & Hot Tub. Your Next Vacation

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
The price is CA $201
CA $263 total
includes taxes & fees
Sep 6 - Sep 7
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
The price is CA $140
CA $275 total
includes taxes & fees
Sep 6 - Sep 7
Cozy 1-bedroom barn in marvelous Hampton with AC

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.
The price is CA $160
CA $562 total
includes taxes & fees
Sep 8 - Sep 9
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

Find out more about Jolliff

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Jolliff. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.