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Townsend Holiday Rentals

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Our top choices for Townsend holiday rentals

1. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is NZ$207
includes taxes & fees
11 Nov - 12 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

2. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is NZ$183
includes taxes & fees
10 Nov - 11 Nov
Country Get Away Studio Apartment

3. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is NZ$521
includes taxes & fees
15 Nov - 16 Nov
Historic Chesapeake City Stay

4. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is NZ$269
includes taxes & fees
3 Dec - 4 Dec
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

5. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is NZ$393
includes taxes & fees
15 Nov - 16 Nov
Nature's Haven Tiny Home

6. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is NZ$494
includes taxes & fees
4 Nov - 5 Nov
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

7. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
9.8 out of 10, Exceptional, (7 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is NZ$491
includes taxes & fees
19 Nov - 20 Nov
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

8. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is NZ$444
includes taxes & fees
4 Nov - 5 Nov
Tiny Home Tranquil Oasis

9. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is NZ$691
includes taxes & fees
1 Dec - 2 Dec
Elegant Family Stay • Quiet Neighborhood • Comfort

10. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is NZ$336
includes taxes & fees
9 Nov - 10 Nov
Turtle Cove Room

11. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is NZ$361
includes taxes & fees
9 Nov - 10 Nov
Beachcomber Suite

12. Long Beach Cottage, (romantic couple’s getaway)

Long Beach Cottage, (romantic couple’s getaway)
Charlestown
10.0 out of 10, Exceptional, (8 reviews)
"Nice, quaint house, right on the water. Perfect for couples looking to relax. "
United States
Mike F.
The price is NZ$819
includes taxes & fees
9 Nov - 10 Nov
Long Beach Cottage, (romantic couple’s getaway)

13. Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
The price is NZ$657
includes taxes & fees
4 Nov - 5 Nov
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

14. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is NZ$479
includes taxes & fees
16 Nov - 17 Nov
Secluded Cottage in Middle of Chestertown

15. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.4 out of 10, Very good, (24 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is NZ$634
includes taxes & fees
8 Nov - 9 Nov
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

16. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is NZ$610
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

17. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is NZ$489
includes taxes & fees
15 Nov - 16 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

18. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (115 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is NZ$901
includes taxes & fees
4 Nov - 5 Nov
Waterfront house with amazing views. Top of the Chesapeake

19. Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge
Charlestown
10.0 out of 10, Exceptional, (5 reviews)
"Had a wonderful stay. They really thought of everything. Had everything we could have possibly needed. It's a beautiful place and it was very clean and cared for."
United States
Laura K.
The price is NZ$732
includes taxes & fees
9 Nov - 10 Nov
Long Beach Wellness Retreat Sauna/Hot Tub/Cold Plunge

20. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (8 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is NZ$642
includes taxes & fees
1 Dec - 2 Dec
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
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 Townsend Hotel Reviews

Find out more about Townsend

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Townsend holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Townsend. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Townsend. Seeing all the best attractions is bound to make you fall in love with Townsend. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Townsend short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Townsend?

Yes, there are holiday rentals close to the most popular sights in Townsend, 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 Townsend has to offer?

Private 3BR Farmhouse on Estate with Event Space, Horses,Trails, Ponds & Orchard: This highly rated holiday home rental in Townsend is located in a rural location, and has a garden, a selection of games 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. Make the most of Access to hot tub in this rental home to help you unwind.

What can I see and do in Townsend?

Explore the area and family-friendly sights such as Frightland, or get out into nature at a spot like Woodland Beach. In the wider area, you’ll find Middletown Town Hall and Middletown Historic District.

What are holiday rentals like in Townsend?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Townsend. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for family gatherings.