Holiday houses in Rehoboth Bay

Luxury Dewey: Rehoboth Bay Front*1 Block to Ocean!

⭐ AWARDED GUEST FAVORITE Luxury Dewey Beach Bayfront Condo – Rooftop Pool | 1 Block to Ocean | Walk to Rehoboth Nauti by Nature – Top-Floor Bay Retreat Experience Dewey Beach from this top-floor condo overlooking Rehoboth Bay — just 1 block to the ocean and minutes to downtown Rehoboth. Wake up to bayfront serenity. Beach by day. Walk to dining, nightlife, and music. Bike to Cape Henlopen State Park. End with sunset views from your balcony. More than a stay — it’s a coastal lifestyle escape!

Coastal 2BR • 10 min to Beach & Trails

Welcome to The Loft, a cozy Rehoboth Beach retreat. Feel right at home in this spacious 2BR, 2BA condo conveniently located East of Rt. 1 between Rehoboth Beach and Lewes Beach. The condo is also just minutes from Junction & Breakwater Trail, Georgetown Lewes Trail and Cape Henlopen State Park... perfect for walks and biking. Love shopping? There are 3 Tanger Outlets and an abundance of other stores. Explore endless dining options in downtown Rehoboth Beach, Lewes and all along Coastal Highway.

Romantic Sunset Suite

5 min walk (0.3 miles) to the beach and ocean, or enjoy your own private bay front beach out your back door, and gorgeous, romantic sunsets. First floor unit boasts a totally private bedroom and bath, and separate entrance. Sleep well on new queen mattress. Park your car and leave it. Located at the quieter south end of Dewey, yet still within walking distance to restaurants, nightlife, water sports, marina. Take Trolley or Uber to nearby Rehoboth for shops, restaurants and boardwalk fun!

Kisa Dove

Kisa Dove is conveniently located East of Rt. 1 at Midway, Rehoboth Beach. This adorable beach cottage is in walking distance to all that Midway has to offer, including restaurants, shopping and entertainment. Midway movie theater, Dunkin Donuts, Acme, Surf Bagel, Panera Bread, 1776 Steakhouse, Marshalls, Midway Speedway and Water Park, and more, are all just within a 10-minute walk. NOTE - this cottage is an upper-level, detached garage apartment. The primary house is owner-occupied.

Luxury Coastal Townhouse with Pool & Game Room

This exquisite 4-bed, 3.5-bath townhouse offers a spacious retreat adorned with contemporary furnishings. The open-concept living area invites gatherings, while the gourmet kitchen, is equipped with modern appliances and sleek countertops. Each of the bedrooms provides a tranquil sanctuary. Outside, a private balcony offers a serene space to enjoy the evening sunsets. With the perfect blend of comfort and coastal charm, our townhouse promises your family an unforgettable beachside getaway.

TOWNSAND 1 block to ocean 1 block to dine/imbibe

Where the city meets the sea. One block to the beach and boards, one block to the best restaurants in Rehoboth. Townsand loft is the perfect location for your stay in Rehoboth. Park the car in the dedicated off street spot in front of Townsand and walk to everything. This light filled home features a designer renovation with exposed rafters, upscale full kitchen, custom bathroom and vaulted ceilings. The sleeping loft makes for a cozy slumber after a day of sun and a night on the town.

Tiny Living: The Blue Bird Tree House 1BR/Den

Tiny Home with mature trees in the middle of the nature but close to the beaches! Tranquil woodsy getaway located on 3 acres of mature trees, 8 miles to beaches, and shopping! The Blue Bird is an older 1950's style tiny cabin on the 2nd floor (locked garage on 1st floor), with 1 bedroom Queen Bed, Den with single bed, 2 baths, fully equipped kitchen, large deck for relaxing. There is an entry exterior door Security Camera for safety. Not suitable for toddlers due to 14 steep stairs.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

Cozy condo / 3,5 miles from the beach.

Cozy condo in a perfect location, close to Rehoboth and Lewes. This is a spacious and bright ground level condo 2bedrooms/2 full bathrooms in Sandpiper Village. Is a perfect spot for having a great time with family, friends or couples. Sandpiper Village its located between Rehoboth Beach (3.5miles) and Lewes (4 miles). Our condo unit includes free parking, full kitchen, living room, dining room, washer/dryer, dishwasher, Youtube TV /wi-fi. We supply sheets and towels.

Boaters And Fisherman Paradise at Massey's Landing

Bring your boat to a Cozy, Retro, Rustic getaway. Situated between the Indian river bay and the Rehoboth Bay. .5 miles from Massey's Landing public boat launch and fishing pier. 17 miles from Rehoboth Beach, with traffic it could take you 45 mins to get to the beach, without traffic about 25 min. The house has 2 bedrooms, and a living room which is open to the kitchen. There is also a large screened-in porch attached. Plenty of room to park your boat.

Beautiful Waterfront Home-Private, Clean, Relaxing

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* and no pets from June 14 to Labor Day.

Mid-Century Milton w/heated Pool

Mid-Century Modern Retreat with Pool – Beaches, Breweries & Parks Unwind in style at this mid-century modern escape at Red Mill Pond. With its private pool, open design, and curated retro décor, the home is as comfortable as it is eye-catching. Perfectly located near the breweries, beaches, and bike paths! 9 mins - Dogfish Brewery 12 mins - Lewes Beach 16 mins - Rehoboth Beach Boardwalk 19 mins - Dewey Beach