Holiday houses in Chesapeake City

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Top-rated holiday rentals in Chesapeake City

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Guest favourite

Apartment in Chesapeake City

4.92 out of 5 average rating, 66 reviews

hygge haven: hygge= happy + cozy

Chesapeake City is a historic town located on the C & D Canal; it's not unusual to be greeted by locals as you explore the town. The apartment is a bedroom with sitting area, fully equipped kitchen & bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a Nespresso machine, coffee pods,sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.

25 Nov – 2 Dec

$287 NZD per night

Guest favourite

Home in Newark

4.83 out of 5 average rating, 6 reviews

White Clay Creek Cottage

Welcome to our cozy cottage retreat in the perfect location of Newark! Nestled against the backdrop of a picturesque horse farm, our 2-bedroom, 1-bathroom cottage offers a serene escape from the hustle and bustle. Come and relax on the furnished deck and you just may see a few horses. The cottage is Pet Friendly and has a fenced in yard to accommodate our furry guests. 5 minutes to Deerfield Country Club, Less then 10 Minutes to downtown Newark, and just a few minutes to White Clay Creek Park.

24–31 Mar

$201 NZD per night

Guest favourite

Guest suite in Newark

4.99 out of 5 average rating, 170 reviews

Spacious, light filled studio 2 blocks from UDel

Our quiet, private studio is located in the historic Old Newark neighborhood, next to the Univ of Delaware, only a few minutes' walk to the center of downtown Newark. Newark is a thriving college town with restaurants, history museum, library, small stores erc. The studio is in a quiet, friendly, safe, historic and walkable neighborhood. If you are looking for privacy and serenity in this charming town, this is the place! Guests describe our studio as immaculately clean, private and calming.

5–10 May

$205 NZD per night

Guest favourite

Home in Rising Sun

4.95 out of 5 average rating, 239 reviews

Home Away from Home in Rising Sun, MD

PLEASE READ: Children under 12 years of age are not suitable for this home. Check in:3-8pm can be flexible to fit your schedule.Check out: 11am This home has a living room, kitchen and dining area, two bedrooms and a full bath. No pets! THE THIRD BEDROOM is a master suite that can be added for an ADDITIONAL CHARGE. It includes a living area, queen bed, bathroom and kitchenette. Ask for more details. This home is very comfy and has a history room from family collectibles dating back to 1854.

18–25 Oct

$246 NZD per night

Guest favourite

Apartment in Havre de Grace

5.0 out of 5 average rating, 100 reviews

Retro Downtown One Bedroom at JoRetro

Indulge in a nostalgic retreat at our renovated mid-century modern apartments in downtown Havre de Grace, situated above JoRetro. Choose from four meticulously decorated units, each inspired by an iconic Pyrex design. Relax on the queen-size bed, with luxury linens, and enjoy retro and vintage items, including Butterprint Pyrex pieces. Explore a variety of restaurants and unique shops, all within walking distance. Don't miss the opportunity to visit the historic Lighthouse and museums.

21–28 Mar

$259 NZD per night

Guest favourite

Apartment in Frederica

4.97 out of 5 average rating, 258 reviews

Smokefree Lakeside Relaxation

Quiet smoke free lakefront Carriage House studio over garage with separate entrance. Mini Fridge, microwave, dishes. Use of fire pits, canoe, SUP, dock. Lake is fishable and swimmable. Flatscreen HDTV with Premium Channels. WiFi to use with your own device or use my laptop in unit. 45 min from beach. 20 minutes to Dover. 4 parks with walking paths within 10 miles. Close to Dover Air Force Base but not in flight path. Well behaved social pets with responsible owners are welcome!

9–16 Sep

$121 NZD per night

Guest favourite

Guesthouse in Chesapeake City

5.0 out of 5 average rating, 149 reviews

High-End Cottage, Water View, Chesapeake City, MD

"Fairwinds Cottage" is a newly renovated coastal themed guest cottage with a water view on the quiet side of the canal in Chesapeake City, Maryland. Enjoy watching the ships pass through the canal, take a walk on the beautiful 17-mile Ben Cardin/Mike Castle Recreational Trail just steps from the house. Walk to Schaefer's Canal House for their amazing crab cakes and libations. Stay with us and learn why Chesapeake City was voted the #1 most charming town in Maryland in 2018.

14–21 May

$393 NZD per night

Guest favourite

Cottage in North East

4.97 out of 5 average rating, 439 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.

19–26 Mar

$205 NZD per night

Guest favourite

Cottage in North East

4.94 out of 5 average rating, 280 reviews

Cottage Just Off North East's Main Street

Our cozy cottage is located just off Main Street in North East, an easy walk to restaurants, shops and pubs. The cathedral ceilings and exposed rafters create an unexpectedly dramatic space you will find warm and inviting. The relaxing back deck looks down toward a creek that flows through the neighboring property. Our cottage is the perfect place to stay when you're on the road for work, or a romantic weekend (or mid-week) getaway.

29 Dec – 5 Jan

$193 NZD per night

Guest favourite

Cottage in Chesapeake City

5.0 out of 5 average rating, 53 reviews

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

9–16 Sep

$411 NZD per night

Guest favourite

Home in Chesapeake City

5.0 out of 5 average rating, 29 reviews

Charming, updated home in Historic Chesapeake City

This historic home is nestled right in the heart of Chesapeake City. With shops, restaurants, and libations literally just around the corner, you'll be pleased to know that you can walk to grab your morning cup'o' joe at Cafe on the Bay or eat, drink, and be merry at one of our many local establishments without having to worry about driving! Weekly discount available.

15–22 Oct

$761 NZD per night

Guest favourite

Apartment in Rising Sun

4.97 out of 5 average rating, 198 reviews

Cross Keys Tavern

Built in 1744, this lovely home is the perfect country getaway. Cozy apartment in a historic property located in the little town of Calvert. Huge master bedroom with plenty of relax room. Private entrance with plenty of parking. Six miles from Fair Hill Natural Resources Area and a golf course practically in the back yard.

11–18 Jan

$253 NZD per night