Tolchester Beach Vacation Rentals

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Dec 6 - Dec 7
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Dec 7 - Dec 8
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Vacation Rentals in Tolchester Beach

Printers
Hudson house

Residence in Canton

3.5 star property
The price is ￥24,081
￥51,596 total
includes taxes & fees
Dec 8 - Dec 9
Hudson house
Fridge, microwave, oven, stovetop
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

Vacation Home in Cape Saint Claire

2.0 star property
The price is ￥46,832
￥89,689 total
includes taxes & fees
Dec 15 - Dec 16
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12
Property grounds
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !

Vacation Home in Pasadena

9.4 out of 10, Exceptional, (89)
"This property was a great place for a family to all relax together, play games, and enjoy the water!"
United States
Armando V.
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
6 bedrooms, iron/ironing board, WiFi, bed sheets
Luxury Waterfront Home Built for Entertaining!

Vacation Home in Abingdon

8.4 out of 10, Very Good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is ￥76,888
￥129,085 total
includes taxes & fees
Dec 8 - Dec 9
Luxury Waterfront Home Built for Entertaining!
Interior
200 steps to the beach!

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (93)
"Beautiful, comfortable home in a great location. "
United States
Stephanie C.
200 steps to the beach!
Property grounds
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit

Vacation Home in Grasonville

10.0 out of 10, Exceptional, (24)
"Place was fantastic!"
United States
larry
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Dining
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Villa in Rock Hall

9.8 out of 10, Exceptional, (40)
"Ashleigh was amazing as a host, got right back to us on all questions and needs. "
United States
Tim B.
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Marina
Cass-N-Reel Luxury Houseboat

Houseboat in Grasonville

10.0 out of 10, Exceptional, (47)
"Amazing views! Location is great, restaurants at walking distance, great bicicle trail, highly recommended!"
United States
Oliver C.
Cass-N-Reel Luxury Houseboat
Property grounds
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is ￥55,919
￥103,236 total
includes taxes & fees
Dec 8 - Dec 9
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

Vacation Home in Glen Burnie

8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is ￥16,915
￥53,989 total
includes taxes & fees
Dec 8 - Dec 9
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Interior
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

Apartment in Annapolis

9.4 out of 10, Exceptional, (36)
"Very communicative host and the in apartment sauna and jacuzzi tub really helped us relax. A great stay overall!"
United States
George H.
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in Arnold

9.4 out of 10, Exceptional, (36)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is ￥20,271
￥50,733 total
includes taxes & fees
Dec 8 - Dec 9
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (39)
"Fabulous place. We’ll be booking again next year. "
United States
Steve R.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Vacation Home in Glen Burnie

8.0 out of 10, Very Good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is ￥13,980
￥19,479 total
includes taxes & fees
Dec 8 - Dec 9
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Interior
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Vacation Home in Bel Air

10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
The price is ￥31,843
￥44,950 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Modern and Cozy Home in Bel Air with a Home Office and Fireplace
Exterior
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Cabin in Chestertown

10.0 out of 10, Exceptional, (12)
"Kayaks were a great plus! Ideal spot for a small family with easy access to the the beautiful Chester River. Our grandchildren had a blast, visiting the pigs, chickens, and sheep that were within easy walking distance."
United States
Douglas N.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Outdoor dining
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

Vacation Home in stevensville

10.0 out of 10, Exceptional, (197)
"This home was the perfect get-away for a group of friends!The accommodations were wonderful and the host went out of their way to ensure our stay was full of fun activities."
United States
David N.
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Terrace/patio
Close to Hospital & White Marsh! Rosedale Townhome

Vacation Home in Nottingham

2.0 star property
The price is ￥26,406
￥81,747 total
includes taxes & fees
Dec 14 - Dec 15
Close to Hospital & White Marsh! Rosedale Townhome
Fridge, microwave, stovetop, dishwasher
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Vacation Home in Chester

10.0 out of 10, Exceptional, (126)
"This house was charming and comfortable. The view was spectacular. Neighbors and friendly. The whole place has a serene feel to it. In addition, the owners were very helpful and responsive. We will be back again!"
United States
Sue R.
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Outdoor dining
BAYSIDE BUNGALOW

Vacation Home in Rock Hall

10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is ￥27,959
￥41,985 total
includes taxes & fees
Jan 4 - Jan 5, 2026
BAYSIDE BUNGALOW
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 Tolchester Beach Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Good stay "
D 3-night trip
Posted 3 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Tolchester Beach

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Frequently asked questions

Can I find a vacation rental in Tolchester Beach?

Yes, we give you a choice of vacation rentals near top points of interest in Tolchester Beach, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Tolchester Beach has to offer?

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This vacation home rental outside of Tolchester Beach is located on the beach and has a fireplace, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What can I see and do in Tolchester Beach?

Northern Chesapeake Bay and Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find The Mainstay and Rock Hall Harbor.

What are vacation rentals like in Tolchester Beach?

Vacation rentals are private accommodations you can reserve for a short or long stay in Tolchester Beach. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for small groups.