Holiday rentals in Jimtown

5 out of 5 average rating, 3 reviews

NEW - Coastal Quarters - Unit 1 -2BR

Relax and unwind at this beautifully renovated and fully furnished 2-story retreat, featuring 2 cozy bedrooms and 2 full bathrooms. Perfect for small groups or couples, this charming getaway offers modern comforts and a peaceful ambiance. Conveniently located near beaches and attractions, it’s an ideal home base for your vacation. (*Please note - this is only the 2 bedroom unit) **Need more space? Rent alongside with Unit 2, the 5-bedroom main house next door with a fenced in backyard oasis!*

4.94 out of 5 average rating, 104 reviews

Guest house in Lewes

Crow's nest! Guest house-bike trail-3.7mi to beach

Lovely 1 bed/1 bath detached upstairs guest apartment. The space provides privacy & convenience to Lewes activities with serene garden landscaping. It boasts beachy decor with locally sourced touches, a fully stocked kitchen, and a beautiful bedroom complete with a desk and a canopy bed to provide guests with the perfect escape. Enjoy al fresco dining under a pergola & lawn games. Just 3.7 mi to Lewes beach: walk or bike to Old World Bread Bakery, Beach Time Distilling & Lewes Brewing Company!

4.98 out of 5 average rating, 133 reviews

Mimi’s Place @ The Villages of 5 Points in Lewes

You will enjoy this 3rd floor (no elevator) renovated condo with amenities-tennis courts, walking & biking paths connecting to downtown Lewes & 2 outdoor pools in season. The condo is east of route 1, 3 miles to Lewes beach & 15+ restaurants, 3 you can walk to (2 blocks away), nail salon, a hair salon, grocery store and a CVS (4 blocks). We need pictures of everyone’s license and the person booking must be at least 25 years of age. 4 beach chairs & umbrella are in closet on outside porch.

4.98 out of 5 average rating, 50 reviews

Water Views * Balcony * Pool * Fast Wi-Fi

Explore scenic Coastal Delaware (all four seasons). ✔ Relaxing views at the mouth of the Rehoboth Bay ✔ Swimming Pool (summer season) ✔ Easy keypad self check-in ✔ Fast Fios Wi-Fi (950/880 Mbps) ✔ Downtown Lewes 7.4 miles ✔ Cape Henlopen State Park 10.2 miles ✔ Rehoboth Beach Boardwalk 6.4 miles ✔ Kayak launch area ✔ Convenient single-level living (1st floor) ✔ Smart TV's w/ cable channels ✔ Reserved parking ✔ Free locally roasted coffee ✔ Marina/boat ramp on-site (Freedom Boat Club)

Superhost

4.86 out of 5 average rating, 168 reviews

Elegant 3-Bedroom Condo in Lewes with Pond Views

You will love this bright open condo, with a vaulted ceiling in the family room.There are gleaming wood floors throughout the main living areas. The large wrap around 3 season room has a large sitting area along with a table for dining with beautiful pond views. The master suite features a large walk in closet and master bath with the guest bedrooms & bathroom on the opposite side. Plantations is a beautiful community with green space, ponds, mature landscaping and walking paths.

4.95 out of 5 average rating, 162 reviews

Tiny home in Lewes

Cozy Woodland Cottage

Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

5 out of 5 average rating, 42 reviews

Loft in Lewes

Lovely loft minutes to downtown Lewes and beaches!

Bright and open loft above our home with private entrance. The studio style space includes a queen bed and queen pullout sofa. Less than four miles to downtown Lewes, Cape Henlopen State Park, and Lewes Beaches. Eight miles to the Rehoboth Boardwalk with so many restaurants and shopping options in between! Eight miles to Dogfish Head Brewery and historic Milton. Bus station is half a mile away and makes a trip to the beach a breeze! So close to many charms of Sussex County.

4.97 out of 5 average rating, 102 reviews

1st Floor Beach-town Condo in Lewes

Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

5 out of 5 average rating, 10 reviews

Flat in Lewes

Bubba & Banjo's

Bubba & Banjo’s was built as a home for me and my husband before we bought our first house. And now we get to share it with others! Luxury garage apartment, barndominium, pole barn are a few words people have used when describing the spot. The garden view might be one of my favorite things but the spacious tile shower is a close runner up! It’s simple but checks all the boxes for what a great rental spot should be in our opinion.

5 out of 5 average rating, 82 reviews

SeaScape - beach, tennis, pickleball, shopping.

We offer you a modern, sophisticated and functional beach vacation/office/work space, that was entirely renovated in 2022. SeaScape is located in between Lewes and Rehoboth Beach in a quiet gated community, minutes to shopping and entertainment, about 5 miles by car from Rehoboth/Lewes Beaches, 8 miles from Cape Henlopen State Park. The community offers ample opportunities for biking, walking, tennis and pickleball.

4.94 out of 5 average rating, 101 reviews

Cozy condo in the Villages of Five Points, Lewes

Located in the Villages of Five Points Lewes, east of route 1, our condo is the perfect spot for your weekend gateway or a family beach vacation. Lewes beach is about 3 miles, biking paths and trails that connect to downtown Lewes are in close proximity. Within walking distance from the property enjoy the restaurants, have a splash in the pool in the summer time, or hit the tennis courts for some fun.

4.95 out of 5 average rating, 191 reviews

Guest house in Lewes

Very private and cozy, Country Cottage

You’ll love my place because of the outdoors space and relaxing country feel. The cottage is best for couples. A maximum of two dogs is allowed. Distances from my place to Cape Henlopen Park (9.9miles), Rehoboth Beach (10 miles), Dewey Beach (11 miles). Tanger Outlets (7.8 miles). Please keep in mind that, although the above distances are accurate, driving time may be longer due to seasonal traffic.

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Popular amenities for Jimtown holiday rentals

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Other great holiday rentals in Jimtown

Private room in Rehoboth Beach

4.83 out of 5 average rating, 315 reviews

Private Guest Room Just Off Route 1

MiriamRating, 5 stars1 week ago

The stay was great. Very clean and great area.

Guest suite in Rehoboth Beach

5 out of 5 average rating, 6 reviews

Kisa Dove

ElliotRating, 5 stars1 week ago

Space was super clean & exactly what we expected. Instructions on how to get there & how to get in were easy to follow. The host was unbelievably kind & gracious. Helped us with any issues or problems we had. Perfect space for two people. If I go back to Rehoboth beach I would want to stay there again.

5 out of 5 average rating, 10 reviews

Villa in Lewes

Coastal Club * 3BR Luxury Villa Townhouse

ArzhangRating, 5 stars4 days ago

House was clean and well lit. Decor was very elegant. Kitchen was fully stocked. Nice beaches within 15 minute drive. Overall area is very nice. The lighthouse club amenities were great, but at the time of this review the restaurant and bar were closed for renovation or management change.

5 out of 5 average rating, 50 reviews

Coastal Farm Cottage

EvanneRating, 5 stars5 days ago

We had amazing time at Chad’s Airbnb. What beautiful surroundings lots of land to walk around. The house was so cute very updated and comfortable. Chad was quick to respond to all questions we had. We would recommend anyone and their 4 legged friends to stay at Chad’s. Evanne and Al Cuccorelli

4.92 out of 5 average rating, 13 reviews

Spacious Lewes Retreat

ShekhinahRating, 5 stars9 months ago

My family of 7 enjoyed the space. Great, spacious backyard. We enjoyed the play set and fire pit. Inside we had plenty of room for sleeping and play. Every time we needed something, we were able to open a closet and find it. Great space and accommodations.

4.9 out of 5 average rating, 10 reviews

Village of 5 Points Lewes Beach Condo 2BR/2B

AmandaRating, 5 stars2 days ago

Chris was an awesome host! very accommodating and his place was beautifully updated. My sister stayed in the same complex and rented outside of airbnb and their place was awful. 100% happy with our condo and our stay was great, even though it rained. we would love to stay again

5 out of 5 average rating, 11 reviews

Your Home Away From HomeLuxury7BR House*Sleeps 14

VarunRating, 5 stars2 months ago

Our stay at Anna's place for six weeks was nothing short of amazing! The house is in fantastic condition, making us feel right at home. When we encountered a minor issue with the TV, Anna promptly addressed it and had it fixed in less than 24 hours—her responsiveness truly set her apart as a host. Communication with Anna was outstanding; she was always available and eager to assist us with any inquiries. Plus, the Coastal Club neighborhood is delightful, offering a great atmosphere for relaxation and exploration. We wholeheartedly recommend staying at Anna's home. It was a pleasure to experience such hospitality. Thank you, Anna, for making our stay so enjoyable!