Photo by Jennifer Crim

Middlesex County vacation rentals

We found 222 vacation rentals — enter your dates for availability

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May 2025

June 2025

Select from 41 homes, 23 cottages, and other vacation rentals in Middlesex County to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the amenities you expect for your stay, which might include WiFi and a hot tub. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Popular Middlesex County destinations on Vrbo

Delicious spot in Urbanna, VA for fresh, local oysters (fished right in front of the property!). The same people that own Rappahannock Oyster Bar in DC own this, I believe.

They have a good wine and beer selection and other tasty dishes like pimento grilled cheese and fresh salads. Definitely worth a stop if you're in the area.

More info here: http://www.badsentences.com/food-merroir/

Vacation rentals with weekly discounts - Middlesex County

Showing deals for:Aug 15 - Aug 22

Exceptional

(25 reviews)

Newly Built Waterfront Home on Galway Bay with Sandy Beach, Dock and Hot Tub.

Kilmarnock, VA

10% off

per night

All fees included

Or leave the cove for the Rappahanock River and Chesapeake Bay

Exceptional

(24 reviews)

Swim, fish, boat or just relax and enjoy the "Rivah Life" at Little Oyster

White Stone, VA

10% off

per night

All fees included

Exceptional

(94 reviews)

WATERFRONT COTTAGE, Only 5 years old, Located on Beautiful Taylor Creek

Weems, VA

15% off

per night

All fees included

Exceptional

(7 reviews)

Cozy little home on Gwynn's Island with semi-private Chesapeake Bay beach access

Gwynn, VA

15% off

per night

All fees included

Exceptional

(5 reviews)

Still Waters Point- Enjoy breathtaking views at our peaceful Gwynn's Island home

Gwynn, VA

15% off

per night

All fees included

All fees included

Exceptional

(7 reviews)

Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach

Hudgins, VA

10% off

per night

All fees included

Wonderful

(25 reviews)

Tipsy Mermaid “Rivah House” Kayak/Paddlebaord/Crabbing/Fishing

Lancaster, VA

10% off

per night

All fees included

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Middlesex County

Step back in time at Historic Rosegill, an 18th century manor house on 700 acres sited on the Rappahannock River at the mouth of Urbanna Creek. With its, 5 bedrooms, expansive grounds, pool, dock and fishing lakes, it has something for everyone.

Historic riverfront farm 700 acres, pool, private lakes, dock

Sleeps 12 · 5 bedrooms · 5 bathrooms

Waterfront River Home- Chesapeake Bay, Deltaville, VA. Pier and private beach

Sleeps 8 · 4 bedrooms · 3 bathrooms

Waterfront 4BR- Private Pier, Kayaks, Fishing, Beautiful Sunrises and Sunsets!

Sleeps 8 · 4 bedrooms · 2 bathrooms

Top rated rentals - Middlesex County

Urbanna Vacation Rental | 3BR | 3.5BA | Stairs Required | 4,467 Sq Ft

Family

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Book a vacation rental for your Middlesex County getaway

Learn about the unique charm of Middlesex County with a stay in a private vacation home. This city has something for everyone. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Middlesex County

Are you hoping to discover attractions to visit during your stay? Venture out of your cozy vacation rental and check out everything that makes Middlesex County a fun spot to vacation. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

Compass Entertainment Complex (11.5 mi / 18.5 km)
Golden Eagle Golf Club (11.8 mi / 19 km)
Saude Creek Vineyard (17.2 mi / 27.7 km)
Kiskiack Golf Club (17.4 mi / 28 km)
Stonehouse Golf Club (17.8 mi / 28.6 km)
Good Luck Cellars (14.9 mi / 24 km)

Exploring the natural landscape of Middlesex County

Whether you're an outdoor enthusiast or just want to take in the scenery, Middlesex County is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

White Stone Beach (11 mi / 17.6 km)
Fossil Beach (14.8 mi / 23.8 km)
Bethel Beach (22.7 mi / 36.5 km)
Bethel Beach Natural Area Preserve (23.1 mi / 37.2 km)
Urbanna Historic District (2.4 mi / 3.8 km)
Holly Point Nature Park (15.3 mi / 24.6 km)

Frequently asked questions

What is the best area to stay in Middlesex County when booking a vacation rental?

Among the most popular areas to choose your Vrbo vacation rental in Middlesex County is Deltaville. Make your home away from home here and discover some must-see attractions, like Deltaville Marina and Deltaville Maritime Museum.

What is the most popular type of vacation rental accommodation in Middlesex County?

The most desirable types of vacation rentals in Middlesex County are cottages. Hoping for something different? Vrbo has a variety of options to match our guests’ requirements, so you’ll see vacation properties in loads of shapes and sizes. The perfect fit is ready and waiting for you — grab yours today.

How much does it cost to rent a vacation rental in Middlesex County?

Property type, season and length of stay are among the factors that can determine the price of a vacation home. Simply add your dates of travel to find the ultimate escape. From cozy cabins to sprawling luxury villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Middlesex County?

Prices for beach houses in Middlesex County will vary depending on the size and style of the property and when you plan to travel. Just enter your travel dates into Vrbo and the number of guests to view your rental options and prices. From there you can use our filters to narrow down your search by ratings, amenities and more.

Are there pet-friendly vacation rentals in Middlesex County?

Yes. There are. You can pick from eight vacation rentals that cater to pets in Middlesex County. Many of our pet-friendly vacation rentals even have a backyard for your furry pal to run around in, special dog beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect digs on Vrbo.

Are there large group vacation rentals in Middlesex County?

With seven properties that can host 10 or more guests in Middlesex County, there’s no need to keep anyone off the invite list. From family vacations to events like birthday parties and weddings, Vrbo will help you find a large group rental to suit the occasion.

Are there one-bedroom vacation rentals in Middlesex County?

You can choose from 7 one-bedroom rentals in Middlesex County. Whether you’re on the lookout for a townhouse or a luxury condo, our one-bedroom properties are great if you don’t require tons of space. One of the perks of having your own digs? You won’t ever have to share your adventure with strangers.

Can I find two-bedroom vacation rentals in Middlesex County?

You can pick from eight two-bedroom vacation properties in Middlesex County. Put your little ones in the second room or maybe fill it with a couple of your besties. There’s ample space for whoever’s fortunate enough to be coming along.

Are there vacation rentals with WiFi in Middlesex County?

Middlesex County has 19 vacation rentals with WiFi, so you can stay connected while traveling. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movie blockbusters to updating your social media, these Vrbo homes make it easy to get online.

How can I find vacation rentals with air conditioning in Middlesex County?

Pick your travel dates and then use the filter tool to locate vacation rentals with air conditioning in Middlesex County on Vrbo. With 34 air-conditioned properties on offer here, you can look forward to a cool and comfortable stay.

How old do you have to be to rent a vacation rental in Middlesex County?

We recommend checking with the Middlesex County vacation home you’re looking at on Vrbo as the age limit differs. However, it’s generally 16, 18 or 21.

How long can I rent a vacation rental in Middlesex County for?

The amount of time you can rent a Middlesex County vacation home for depends on the property. Just enter your dates of travel to view options offering extended stays. They feature everything you need to make your extended break more comfortable and convenient, such as kitchens and laundries. Some Vrbo vacation rentals may also offer weekly or monthly discounts, so you can stay longer for less money.

Does Vrbo offer discounts for vacation homes in Middlesex County?

On Vrbo, we’ve got plenty of incredible deals and discounts for Middlesex County. Check out our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you’re looking for a mini getaway or a longer stay, Vrbo offers lots of options for all styles and budgets.