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Townsend Holiday Rentals

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Holiday Rentals in Townsend

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Historic Chesapeake City Stay
8.0 out of 10, Very good, (1)
"The place overall is very simple and nice. The bed was a little uncomfortable And decided to not stay the extra night and come home and use my own bed. Overall, very clean very nice."
The price is NZ$387
includes taxes & fees
4 Jun - 5 Jun
Historic Chesapeake City Stay
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (19)
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
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350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (27)
"This location was perfect for our stay during a bass tournament on the upper bay. boa parking was great and very secure compared to hotels. SAhelly was very accomadating"
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Retreat Near Dover
10.0 out of 10, Exceptional, (1)
"This house was the perfect affordable option for a coaching staff taking a team to the DE sport complex. Way more affordable than the hotels in the area and definitely cleaner. Beautiful field view in the back yard that reminded us of home. Will definitely go back!"
The price is NZ$741
includes taxes & fees
10 Jun - 11 Jun
Retreat Near Dover
Family-Friendly Cottage, Walk to the Beach!
10.0 out of 10, Exceptional, (14)
"Great location "
Family-Friendly Cottage, Walk to the Beach!
Waterfront house with amazing views. Top of the Chesapeake
10.0 out of 10, Exceptional, (89)
"Our Family decided to take a last minute Spring Break trip and had a fantastic time. Matt was a great host and easy to communicate with. We were pleasantly surprised by all of the local dining options. Despite terrible weather that we experienced, we made the best of our trip and had a great time."
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (34)
"Great view awesome living space and easy access. Thank you."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Rambling Victorian Beach House on Maryland's Eastern Shore
10.0 out of 10, Exceptional, (13)
"Our group of couples + kids enjoyed our getaway to the Eastern Shore. Betterton was a great home base to visit our alma mater, Washington College, in Chestertown. There, we visited the farmers market and waterfront park & playground with the kids. Back in Betterton, the house fit our group well. Plenty of bedrooms, bathrooms and space for each family. The kids & adults enjoyed spending time lounging in the third floor living room. We were pleased that the house had plenty of games, kids toys,...
Rambling Victorian Beach House on Maryland's Eastern Shore
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
9.6 out of 10, Exceptional, (154)
"The property was beautiful and just as described. The property managers were quick to respond and very helpful. We truly enjoyed our stay."
Riverfront Retreat: Panoramic water views with Hot Tub. Sleeps 16.
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (88)
"We always look forward to our stay at "Betsys Place"! Very clean, super comfy beds and lovely spacious backyard to relax in! Well appointed kitchen. Very quiet street, we always rest well here and enjoy our stay. Very close proximity to Fair Hill Natural Resource Area trailheads and stables."
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Private pier and pool at this waterfront Chestertown home
9.8 out of 10, Exceptional, (22)
"We stayed at Peir Pleaseure for Washington college homecoming weekend. We had a BBQ by the pool for our son and his friends. We enjoyed the views of the Chester Riiver from the pier. The house was clean and easiliy accomodates 2 families ."
Private pier and pool at this waterfront Chestertown home
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Chesapeake City Overlook: Breathtaking View!
10.0 out of 10, Exceptional, (3)
"A wonderful place for all 6 of us adults to stay for a fun filled weekend for a family wedding. Beautifully done, well appointed house with an awesome view! It borders the canal trail, a five minute walk to the bike rental, and a great place (Schaffer’s) for dinner and entertainment. Our hostess was prompt, available at just a text message away. I will seriously plan to book again if I return. Nothing in this house was left undone and there was nothing that we needed that we didn’t have. Thanks...
Chesapeake City Overlook: Breathtaking View!
BEACH WITHOUT THE BUSTLE
10.0 out of 10, Exceptional, (21)
"We needed tranquility after returning from a deployment in the Mideast. All was perfect for my team and I."
BEACH WITHOUT THE BUSTLE
Blue Room in Delaware
8.0 out of 10, Very good, (1)
"If you are looking for just a room at a reasonable price, this is for you. The bathroom is very tiny and in need of a remodel. The bedroom and bath were both very clean. The bed was comfortable, but the pullout single bed is not at all. Most pullouts aren’t, but this goes to a new level. This unit was fine for myself for a couple of nites because I was looking for an inexpensive option. But when my 15 yr old son spent the last nite there with me, I got the pullout which was not good at all. I...
Blue Room in Delaware
Guest Suite for up to 2 in a Victorian on the Chester River
The price is NZ$204
includes taxes & fees
10 Jun - 11 Jun
Guest Suite for up to 2 in a Victorian on the Chester River
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See all available properties in Townsend
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.

Other types of properties in Townsend you may be interested in

Bally's Dover Casino Resort
4.0 star property
8.6 out of 10, Excellent, (1355)
"Wonderful "
The price is NZ$151
includes taxes & fees
5 Jun - 6 Jun
Bally's Dover Casino Resort
Sonesta Select Newark Christiana Mall
3.0 star property
7.8 out of 10, Good, (1008)
"I had a little stupid something happen in regards to my room (a self caused issue), that left me locked out of my room. The staff was nothing but understanding & even offered me a side room until the problem was resolved. Thanks so much for everything!"
The price is NZ$198
includes taxes & fees
1 Jul - 2 Jul
Sonesta Select Newark Christiana Mall
Hilton Wilmington/Christiana
4.0 star property
8.8 out of 10, Excellent, (1002)
"They have a gorgeous center court to enjoy. First floor had direct access to it from room. Very relaxing after a long day on the road!"
The price is NZ$229
includes taxes & fees
4 Jul - 5 Jul
Hilton Wilmington/Christiana
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.

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?

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : This holiday home rental outside of Townsend is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Townsend?

Explore the area and family-friendly sights such as Vince's Sports Center, or get out into nature at a spot like Lums Pond State Park. In the wider area, you’ll find C and D Canal Museum and Woodland Beach.

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.

Recent reviews of Townsend properties
Expedia verified reviews