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Townsend Holiday Rentals

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Check prices for these dates

Tonight
27 Jul - 28 Jul
Tomorrow
28 Jul - 29 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Holiday Rentals in Townsend

Chesapeake Bay House with Dock & Private Beach
Relax on the lakeside deck with a round table and four Adirondack chairs, surrounded by a rocky shoreline and a wooden pier.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (165)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Guests can enjoy a serene lakeside experience from this picturesque pier, featuring a table and chair for a peaceful retreat.

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (6)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cabin close to Fair Hill on horse farm
Interior

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
The price is HK$3,579
HK$4,909 total
includes taxes & fees
29 Jul - 30 Jul
Charming 2-bedroom cabin close to Fair Hill on horse farm
Nancy’s Touch, A Waterfront Paradise!
Stroll through the serene garden, featuring a picturesque arborway, vibrant flowers, and a birdhouse, surrounded by a tranquil body of water.

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (164)
"Fully stocked. Clean. Well maintained B-U-TEE-FULL property. Great, quite, private location close to anything you may need. The views are amazing. The hosts are great..."
Nancy’s Touch, A Waterfront Paradise!
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Enjoy a serene beach experience with access to the ocean via the public pier.

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (53)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Relax in a serene hot tub surrounded by lush greenery and a tranquil view.

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"Great place for a quick getaway - enough room for our family of 4 plus a dog to stay comfortably. Beautiful views! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Escape to a serene cabin surrounded by lush greenery and natural beauty.

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Historic Chesapeake City Stay
Enjoy waterfront views from the dock and outdoor seating area, situated near a scenic bridge and lush green surroundings.

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is HK$848
HK$2,188 total
includes taxes & fees
28 Jul - 29 Jul
Historic Chesapeake City Stay
Nature's Haven Tiny Home
Enjoy al fresco dining and relaxation on this serene outdoor deck with a barbecue grill and comfortable seating.

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is HK$1,484
HK$1,841 total
includes taxes & fees
28 Jul - 29 Jul
Nature's Haven Tiny Home
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

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

9.8 out of 10, Exceptional, (8)
"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
Historic Downtown Garden Oasis with Private Patio
Stroll through the serene garden, surrounded by lush plants and a majestic tree.

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (35)
"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
Captivating Chesapeake experience
Relax on the pier with a view of distant landforms.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (269)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience
Walk to Town & River: Charming Home in North East!
Fridge, microwave, stovetop, dishwasher

Walk to Town & River: Charming Home in North East!

10.0 out of 10, Exceptional, (2)
"Great stay and responsive host. So definitely stay again. "
Walk to Town & River: Charming Home in North East!
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis
Pool

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 HK$986
HK$1,682 total
includes taxes & fees
4 Aug - 5 Aug
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Simple, two-story building with a flat roof, surrounded by trees in a tranquil setting.

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (54)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Modern kitchen with white cabinetry, black stove, and microwave.

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Enjoy cooking in this well-equipped kitchen with a central island and bench, featuring stainless steel appliances and ample cabinetry.

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (44)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Escape to a charming cottage surrounded by lush greenery and trees, with a cozy porch and a brick chimney.

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
Waterfront house with amazing views. Top of the Chesapeake
Relax on the deck with Adirondack chairs and enjoy the serene lake view.

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (98)
"The water views, sunrises, and many local birds, including a nearby osprey nest, were all spectacular. The whole back of the house is a bank of windows (living room and master bedroom). It feels private as your view is just your outdoor lounge area, dock, and the water. No big downsides (minorly need space for tooth brushes as the sinks are mostly the sink bowls). Everything was clean,and comfortable. In similar off the beaten path vrbo's we've had lower cleanliness or ants, but not here! ...
Waterfront house with amazing views. Top of the Chesapeake
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

Red Roof Inn PLUS+ Wilmington - Newark

Red Roof Inn PLUS+ Wilmington - Newark

10/10 Excellent
"Clean. Room "
To 1-night trip
Posted 1 day ago
Red Roof Inn PLUS+ Wilmington - Newark

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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Townsend is located on the beach, and has a fireplace, a patio and a BBQ 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 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.

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 Earleville Wildlife Management Area. In the wider area, you’ll find Middletown Town Hall and Historic Houses of Odessa.

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.