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Townsend Vacation Rentals

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Jul 14 - Jul 15
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Jul 25 - Jul 27

Vacation 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, (162)
"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, (5)
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 CA $628
CA $861 total
includes taxes & fees
Jul 16 - Jul 17
Charming 2-bedroom cabin close to Fair Hill on horse farm
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Enjoy a serene sea view from this inviting space with a wooden ceiling, glass door to a deck, and a cozy seating area.

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (177)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
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, (163)
"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!
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, (51)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
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)
"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "
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, (4)
"My kids and I absolutely loved our stay at the Outlook! So peaceful and relaxing. We spent a lot of time walking around the trails spotting deer and toads. We did a good amount of fishing on the dock, catching catfish. I hope to stay here again in the future."
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
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, (40)
"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
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Ultimate Retreat @ Papermill Rd
Equipped with a microwave, oven, and dishwasher, this kitchen offers a window for natural light and a clean, contemporary design.

Ultimate Retreat @ Papermill Rd

9.0 out of 10, Wonderful, (6)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd
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 CA $259
CA $321 total
includes taxes & fees
Jul 15 - Jul 16
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, (7)
"Located in a quite area and the host were incredible"
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE
Captivating Chesapeake experience
Relax on the pier with a view of distant landforms.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (266)
"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
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, (42)
"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
Luxury Lake House Getaway in charming Jersey Shore Countryside
Relax on the deck with a view of the serene lake and forested shoreline.

Luxury Lake House Getaway in charming Jersey Shore Countryside

10.0 out of 10, Exceptional, (5)
"Great property, great stay. Loved every detail of the house. Thank you! "
Luxury Lake House Getaway in charming Jersey Shore Countryside
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
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
Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!
Cozy retreat with a large bed, bedside table, and window view.

Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!

10.0 out of 10, Exceptional, (3)
"Exceptional rental. So many spots to gather with friends. Pool was clean and refreshing. The landscape was gorgeous. The lake was tranquil. The kitchen was well stocked with everything we needed. Seven women wanting a peaceful retreat. Your home exceeded our expectations. Thank you for having us!"
Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!
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)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
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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Frequently asked questions

Can I find vacation rentals in Townsend?

Yes, we give you a choice of vacation rentals close to popular sights in Townsend, or you can go with a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Townsend?

Chesapeake Bay House with Dock & Private Beach: This vacation home rental near Townsend is located on the beach and has a fireplace, a patio, and a barbecue grill 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 and your friends and family can relax into your vacation with amenities like 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 larger area, you’ll find Middletown Town Hall and Historic Houses of Odessa.

What are vacation rentals like in Townsend?

Vacation rentals are private properties you can reserve for a couple days or more in Townsend. Vacation rentals feature extras such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for small groups.