Photo by Patricia Knorr

Chester Holiday Rentals

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Holiday Rentals in Chester

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (8)
"Overall it was a wonderful stay for me and 4 of my friends. Plenty of space for everyone to spread out and enjoy the wonderful view of the water while we were between wedding events. The home was off the beaten path, which added to the relaxing feeling of the house. Also it was never more than a 20 min drive to get to our events accross the island. The host was very responsive and more than accommodating for my group. The only very minor suggestion I'd like to make is that the trash in the...
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (17)
"We had a great stay at the Turning Point! We had a great time playing Cornhole, pickleball, basketball, cooking on the grill, cooling off in the pool, and watching football on the big screen TV. House was very clean and comfortable. Would definitely stay again and would highly recommend it to anyone."
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
The price is AU$533
includes taxes & fees
1 Oct - 2 Oct
Cass-Away Luxury Houseboat
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (198)
"While the cottage may have some of the historic/ older quirks, it is a wonderful (and beautiful ) property that we would highly recommend! We loved the walk-ability to downtown Annapolis and the Naval Academy. Despite its close location, it’s quiet at night lending to a good nights sleep 😊. The owner provided us some great insight on the location as well. "
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (47)
"Great house qoth ocean view"
Charming Annapolis WaterVIEW Home
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (29)
"Ideal vacation for family of 22. It suited everyone."
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (199)
"Couples getaway weekend to Annapolis. This was the perfect place to have our Basecamp. Absolutely beautiful location, quiet, and peaceful and easy to get everywhere!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (29)
"Perfect for a 3 day visit! "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is AU$1,200
includes taxes & fees
1 Oct - 2 Oct
Waterfront Cottage on the Eastern Shore
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (76)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (16)
"Beautiful house in great location! It was the perfect house for our annual trip (group of 10 friends) to Annapolis! It was spacious, clean, and well equipped with everything you need in a rental house. Eric and team were super responsive and accommodating! Highly recommended! Will definitely come back next year!"
The price is AU$1,286
includes taxes & fees
30 Sept - 1 Oct
3 Story Stunner in Murray Hill <1 mile from USNA!
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.4 out of 10, Exceptional, (10)
"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (52)
"We had a wonderful stay at this beautiful home! Our Navy football weekend could not have been better. This is the perfect place for eight people to gather. The home is spotless and we all appreciated having such a nice place to relax and visit for the weekend. We really enjoyed the spacious and comfortable backyard seating as well as the kitchen/living room spaces. Being able to walk to the stadium for the game and into town for shopping and dining was a real plus. It was a pleasure dealing...
Recently Renovated Annapolis Home - Conveniently Located
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (7)
"Great property. Close to USNA but away from the craziness of town. House was adorable and very clean. The hot tub was a big hit. "
The price is AU$855
includes taxes & fees
30 Sept - 1 Oct
Charming Cottage with Hot Tub 1 Block from the Bay
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (279)
"Would definitely stay again, host was very kind and house was perfect."
The Heron's Nest at Atlantic Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (105)
"The only downside and it was miniscule in relation to the overall experience was the amount of debris on the front porch that came from storms blowing off of the trees. Couldn't really be helped and again very minor issue. The rest of the house was fabulous!!"
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
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Other types of properties in Chester you may be interested in

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1665)
"In the heart of the historic district. Easy walk to the harbor or Navsl Academy. Lots of shops and restaurants nearby"
The price is AU$284
includes taxes & fees
27 Oct - 28 Oct
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (999)
"I used this hotel as our stay hotel for my boys who shipped to bootcamp. It is across from the Annapolis mall and has restaurants in walking distance. The rooms are beautiful and spacious."
The price is AU$173
includes taxes & fees
23 Oct - 24 Oct
Crowne Plaza Annapolis, an IHG Hotel
Graduate by Hilton Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1001)
"Valet Jim H :) was awesome!! Every afternoon and evening he would be extra friendly when we were going out for dinner and when we came back for the night. Super guy!"
The price is AU$296
includes taxes & fees
30 Sept - 1 Oct
Graduate by Hilton Annapolis
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.

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfront and seafood restaurants. Make sure you have time to check out the golf courses while you're in the area.

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

Rockhold Creek Cottage, Water Front, Vacation Home, Docks: This holiday home rental outside of Chester is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Chester?

Choose from 9 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Explore the area and family-friendly sights such as Annapolis Maritime Museum, or get out into nature at a spot like Matapeake State Park. Chesapeake Bay Environmental Center and Eastern Neck National Wildlife Refuge are a couple of places you'll find in the wider area.

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 provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips or small group gatherings.