Chester Holiday Rentals

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Our top choices for Chester holiday rentals

Charming 2-bedroom home, with lake access, in the Richmond metro area.

Charming 2-bedroom home, with lake access, in the Richmond metro area.
Quinton
10.0 out of 10, Exceptional, (15 reviews)
"We only stayed one night, but we will look to stay again."
United States
Jim J.
The price is NZ$347
includes taxes & fees
13 Apr - 14 Apr
Charming 2-bedroom home, with lake access, in the Richmond metro area.

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now
Lanexa
10.0 out of 10, Exceptional, (3 reviews)
"First and foremost, the property was excellent! The host, Michael was extremely welcoming and kind. The property is in top condition with new everything! The seclusion and lakefront location was to die for. Highly recommend this property as we will be back! "
United States
Kelly B.
The price is NZ$1,278
includes taxes & fees
14 Apr - 15 Apr
4-bedroom waterfront homestead near Williamsburg with WiFi, AC. Book now

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (230 reviews)
"Truly unique, perfectly appointed, cozy and warm with stunning views. A very special experience."
United States
Kristin K.
The price is NZ$367
includes taxes & fees
13 Apr - 14 Apr
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (115 reviews)
"2nd time staying at this property and definitely won’t be the last! Amazing location and great host."
United States
Alexis S.
The price is NZ$367
includes taxes & fees
13 Apr - 14 Apr
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.2 out of 10, Very good, (14 reviews)
"The location was excellent as it was central to a lot of places. Raymond was very quick to respond whenever I reached out. Accessing the house was easy. Very quiet neighborhood, besides the fact that everyone speeds on the street that runs along side of the house in case you have children with you. "
United States
Cindy M.
The price is NZ$500
includes taxes & fees
13 Apr - 14 Apr
Luxury Stay! 10 min away from Fort Lee.

Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Capt. Ron has a charming, welcoming, and delightful alternative to a standard hotel room on offer here. Super fun!"
United States
Robert
The price is NZ$511
includes taxes & fees
12 Apr - 13 Apr
Cookie B

The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (4 reviews)
"Had a great stay while fishing the james river. "
United States
Travis D.
The price is NZ$273
includes taxes & fees
13 Apr - 14 Apr
The Farmhouse Retreat

Cozy 1BR Apt Private Balcony, Gym, Yoga, Pool & Co-Working Space

Cozy 1BR Apt Private Balcony, Gym, Yoga, Pool & Co-Working Space
Old Town Manchester
The price is NZ$523
includes taxes & fees
11 Apr - 12 Apr
Cozy 1BR Apt Private Balcony, Gym, Yoga, Pool & Co-Working Space

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (65 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is NZ$312
includes taxes & fees
13 Apr - 14 Apr
The Studio@ Eanes Drug

Historic Haven in Church Hill

Historic Haven in Church Hill
Church Hill
10.0 out of 10, Exceptional, (62 reviews)
"Excellent accommodations!Great walkable location near local cafes & restaurants with a friendly neighborhood vibe."
United States
Patricia N.
The price is NZ$332
includes taxes & fees
12 Apr - 13 Apr
Historic Haven in Church Hill

Red Juniper Retreat

Red Juniper Retreat
New Kent
10.0 out of 10, Exceptional, (26 reviews)
"Excellent!"
United States
H
The price is NZ$1,003
includes taxes & fees
13 Apr - 14 Apr
Red Juniper Retreat

Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (4 reviews)
"Great spot to spend the evening while traveling through! Comfortable space.Host was very helpful through the check in process and my stay.Thanks Pamela!"
United States
Shawn P.
The price is NZ$318
includes taxes & fees
9 May - 10 May
Newly finished basement suite in Midlothian. Very clean and spacious.

Relax in beautiful second floor apartment with balcony & private fenced yard.

Relax in beautiful second floor apartment with balcony & private fenced yard.
Northern Barton Heights
The price is NZ$646
includes taxes & fees
13 Apr - 14 Apr
Relax in beautiful second floor apartment with balcony & private fenced yard.

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Northern Barton Heights
9.6 out of 10, Exceptional, (16 reviews)
"I loved it 100% recommend "
United States
Milton O.
The price is NZ$691
includes taxes & fees
22 Apr - 23 Apr
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking
Northern Barton Heights
10.0 out of 10, Exceptional, (4 reviews)
"Such a fun place to stay! Room is nicely decorated. Easy check in/check out. Never stayed in this part of RVA before. We will definitely stay here again!"
United States
Teresa M.
The price is NZ$379
includes taxes & fees
13 Apr - 14 Apr
Colorful private guesthouse in charming Richmond with Parking

Earth & Ember -Cottage House Retreat!

Earth & Ember -Cottage House Retreat!
North Highland Park
The price is NZ$467
includes taxes & fees
23 Apr - 24 Apr
Earth & Ember -Cottage House Retreat!

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (33 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
The price is NZ$551
includes taxes & fees
15 Apr - 16 Apr
Downtown Living in Richmond's Amazing Shockoe Bottom

Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
10.0 out of 10, Exceptional, (8 reviews)
"The host was very responsive to any questions I had, responding within a few minutes each time. The space was as advertised with all needed amenities. "
United States
David W.
The price is NZ$549
includes taxes & fees
11 Apr - 12 Apr
Charming 1-bedroom suite with WiFi and AC in Bon Air

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Byrd Park
8.8 out of 10, Excellent, (16 reviews)
"The location was great, lots of shops and restaurants. Quiet street. Lots of beds"
United States
Nathan R.
The price is NZ$458
includes taxes & fees
21 Apr - 22 Apr
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

Midlothian 3 Bedroom getaway for up to 8 guests!

Midlothian 3 Bedroom getaway for up to 8 guests!
Midlothian
9.6 out of 10, Exceptional, (20 reviews)
"Great place to stay. "
United States
Brian K.
The price is NZ$930
includes taxes & fees
16 Apr - 17 Apr
Midlothian 3 Bedroom getaway for up to 8 guests!
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 Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as NZ$312 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 Chester 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 Chester holiday.

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

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Iron Bridge Sports Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Chester. Make sure you have time to check out the art and cafés during your trip.

What are some of the best holiday rentals that Chester has to offer?

Cozy walkable downtown retreat, 3 minutes to VCU: This holiday home rental outside of Chester is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chester?

With 8 Expedia holiday rentals, you're guaranteed to find just the right place for your Chester stay.

What’s there to see and do in Chester?

Family-friendly attractions include Iron Bridge Sports Park and The Lazy Daisy, whereas James River and Henricus Historical Park are a couple of great spots to enjoy the outdoors. Point of Rocks Park and Appomattox River are other places to visit while you're in town.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for a small group gathering.