Holiday Rentals in Templeville

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Holiday Rentals in Templeville

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (13)
"This was a wonderful house for our family gathering. We enjoyed watching the birds, fish, and wildlife from the glassed-in porch. We cooked in the well appointed kitchen and we kayaked too. Evolve staff was top notch all around."
Pet-Friendly Home on Chester River w/ Dock!

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (20)
"a great place to unwind. "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
The price is €226
includes taxes & fees
3 Sept - 4 Sept
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (95)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is €140
includes taxes & fees
14 Aug - 15 Aug
First Floor Studio Apartment in Historic Chestertown

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (81)
"Loved our stay!"
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is €390
includes taxes & fees
18 Aug - 19 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Peaceful country home away in the wilderness

10.0 out of 10, Exceptional, (17)
"Kids were comfortable and well accommodated. Place is nestled back behind the pastures."
Peaceful country home away in the wilderness

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (60)
"We had a fantastic time- the location on the water was gorgeous and loved the hot tub and pool. Extremely quiet and private!"
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (11)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Spacious 5 Bedroom w/Pool, Patio and Theater

9.8 out of 10, Exceptional, (7)
"Great house for a large family "
The price is €761
includes taxes & fees
4 Sept - 5 Sept
Spacious 5 Bedroom w/Pool, Patio and Theater

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

10.0 out of 10, Exceptional, (14)
"Place was newly decorated, very clean, very comfortable. It had all the amenities listed, a comfortable bed and was just very pleasant."
The price is €153
includes taxes & fees
18 Aug - 19 Aug
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (17)
"Communication was excellent, property was super clean and well stocked. Beautiful decor close to the quaint downtown Chestertown. We would definitely stay here again if back in the area."
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

10.0 out of 10, Exceptional, (5)
"We stayed at the property while all our children were at a tournament at the DE turf fields. It was convenient and very comfortable. The house was well supplied and maintained."
Bungalow by the Bay. Minutes to DE Turf Fields. 30 minutes to resort beaches.

The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

10.0 out of 10, Exceptional, (3)
"We rented for my daughter’s graduation from Washington college. Wonderful home that was decorated great with a perfect location!!! "
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (20)
"Perfect setting for our family get together. Plenty of space and beautifully decorated. Spent most of our time on the screened in porch.Beautiful sunset in the evening and lovely view of the river.Several family members used the kayaks and enjoyed the experience.Host was very helpful and went all out to make sure we had everything we needed."
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

10.0 out of 10, Exceptional, (1)
"We had a great stay. Property was updated, clean and in a nice part of town walkable to everything. We would definitely stay here again and are looking forward to it."
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Relaxation Haven on the Shore near Choptank River

9.2 out of 10, Wonderful, (7)
"The property is very quiet and peaceful! No issues at all! Helen was wonderful and very kind!"
Relaxation Haven on the Shore near Choptank River
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 Templeville Hotel Reviews

Frequently asked questions

Can I find holiday rentals in Templeville?

Yes, there are holiday rentals close to the most popular sights in Templeville, or you can select a more secluded option if you're looking for a relaxing stay.

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

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.: This holiday home rental outside of Templeville is located on a river, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What’s there to see and do in Templeville?

While exploring the area, visit family-friendly sights like Crumpton Auction, or get outside and enjoy nature at Silver Lake Park. In the wider area, you’ll find Tilmon's Island Winery and Air Mobility Command Museum.

What’s a holiday rental in Templeville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Templeville. Holiday rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for families.