Vacation rentals in Massey

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Top-rated vacation rentals in Massey

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Deale

4.97 out of 5 average rating, 29 reviews

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Guest favourite

Cottage in Rehoboth Beach

4.9 out of 5 average rating, 110 reviews

Dog friendly, Close to outlets, fire pit, Sleeps 6

Tucked away in a quiet neighborhood, this adorable cottage awaits your next peaceful vacation. With 3 beds/2 baths, there’s space to enjoy a relaxing stay for up to 6 guests with cozy blankets and beds as well as beautiful surrounding gardens. We are only 4 miles to the beaches, 1 mile to outlet shopping, and close to amazing restaurants. You may not even want to leave the cottage at all. Pet friendly (1 dog please). NEW FOR 2024: beautiful bathroom updates and NEW comfy mattress in the master!

Top guest favourite

Condo in Rehoboth Beach

4.96 out of 5 average rating, 160 reviews

Classy Beach Getaway

Our condo is close to everything: Outlet shopping, Entertainment (water park), Biking trails, A pool and jacuzzi on the property, Downtown shopping, some of the best restaurants in Delaware, great views, art and cultural activities. You’ll love it because of the new and IMMACULATE decor, the overall ambiance and the location! It's great for couples, girlfriend getaways, business travelers, and families with older kids :). PLEASE NOTE, during the summer season we only book full weeks.

Guest favourite

Cottage in Pasadena

4.88 out of 5 average rating, 124 reviews

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Guest favourite

Apartment in Rehoboth Beach

4.96 out of 5 average rating, 73 reviews

Chic DT apartment with hot tub, walk everywhere

Enjoy a stylish experience at this centrally-located place. Walk to everything—beach, restaurants, shopping—and enjoy the very best of Rehoboth without ever looking for a parking spot. This newly renovated first floor private apartment of a 3-story house is spacious and loaded with every amenity, including all linens (a rarity in Rehoboth!), local coffee, a well stocked pantry, 65-inch TV with sound system, and your own private patio with dining space, grill, and hot tub.

Superhost

Apartment in Rehoboth Beach

4.82 out of 5 average rating, 17 reviews

Penthouse Place

Experience luxury in this newly renovated top-floor condo. White noise machines, plush pillows and mattresses ensure uninterrupted sleep while the cozy screened-in porch offers serene pond views. Relax in plush seating, enjoy modern amenities, and rest easy in comfortable bedrooms. Conveniently located in the highly sought after Creekwood community, it is near dining and entertainment options, this condo offers the perfect blend of luxury and tranquility for your getaway.

Superhost

Home in Georgetown

4.78 out of 5 average rating, 18 reviews

Salty Roots Ranch_Sports@Beach_DETurf_Dogfish

Escape to Salty Roots Ranch, a spacious 5-bedroom retreat in Georgetown, Delaware, perfect for large groups. Unwind in two cozy living areas or enjoy the expansive backyard with games. Located just 5 minutes from Sports at the Beach, it's ideal for tournament stays. Explore historic Milton, sip craft brews at Dogfish Head Brewery, or relax on Rehoboth Beach, just a short drive away. Whether for sports, adventure, or relaxation, this getaway has it all—book now!

Top guest favourite

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favourite

Condo in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Superhost

Home in Rehoboth Beach

4.93 out of 5 average rating, 15 reviews

So close 2 everything… you’ll never want to leave!

This townhome with 3 bedrooms and 3 1/2 baths is ideally located so that you are only a 5 minute bike/ride/drive to EVERYTHING! Close to the beach/boardwalk, hiking/biking trail, waterpark, breweries, restaurants, outlets, shopping and more! This unit has been fully updated with a contemporary chic beach decor. Ultra-soft bed sheets and towels will make you want to stay forever! 5 star rating on VRBO… book with confidence!!!

Guest favourite

Home in Lewes

4.96 out of 5 average rating, 129 reviews

Woodsey Beach House - Beach, Lake, Woods!

Beach? Check Cabin? Check Lake? Check Have it all at our home near the beach, in a beautiful wooded setting with a lake view! Quiet neighborhood makes you feel right at home. Newly renovated with new appliances and furnishings. The house has an upside-down layout, so most of the living spaces, including the kitchen, dining, and living rooms are on the second floor. The home is unique, bright and comfortable.

Superhost

Cottage in Rehoboth Beach

4.73 out of 5 average rating, 44 reviews

Hidden Pines in Downtown Rehoboth w/Private Yard

Everyone loves Hidden Pines, our charming cottage with a shady landscaped private yard in downtown Rehoboth Beach. Hidden Pines is just off the main street and half a mile from the beach, in a quiet, shady neighborhood. Perfect for a couple or small family, romantic retreat or solo getaway. Our yard is great for relaxing with a good book or entertaining friends. The downstairs was newly renovated Spring 2022.