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Vacation rentals in Greenwood

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Top-rated vacation rentals in Greenwood

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Tiny home in Cambridge

4.89 out of 5 average rating, 496 reviews

Blackwater Tiny Cabin on Snakehead Creek

The Solar Powered Tiny Cabin is located on a farmette 5 min away from Blackwater Refuge! It is an affordable and unique way to visit and enjoy all that Cambridge and Blackwater Refuge have to offer! Staying the cabin will make your visit even more memorable!The Tiny Cabin is now located 50 steps away from Pitcher Dam Creek which leads to the Little Blackwater! Kayaks on site! Bring your fishing rod to catch popular Snakeheads! 15 minute drive to Route 50, downtown Cambridge, shopping and dining!

Nov 19 – 26

R1,641 ZAR per night

Apartment in Greenwood

4.97 out of 5 average rating, 479 reviews

Beach Highway Hobby Farm

We are a hobby farm with pygmy goats and free-range hens located along Beach Highway near Greenwood, Delaware, in the heart of the Mennonite Community (not to be confused with the Amish). We are centrally located in southern Delaware with many attractions within easy driving distance: Rehoboth Beach (35 minutes) Delaware State Fairgrounds (10 minutes) Dover Downs/Firefly (30 minutes) Ocean City, MD (50 minutes) Cape May/Lewes Ferry Terminal (30 minutes) DE Turf Sports Complex (20 minutes)

Nov 17 – 24

R1,601 ZAR per night

Apartment in Magnolia

4.95 out of 5 average rating, 119 reviews

Perfect Rental for Dover Attractions & BayBeaches

15 minutes from Dover Nearby casinos, beaches, and the racetrack. Bowers and Slaughter beaches are about 10-15 mins from us, whereas, the major beaches like Rehoboth, Lewes and Dewey are 45mins to an hour from us. We are 5 mins from Highway 1 and located 15 mins from DE Sports Complex 10 mins from Highway 13 (Dupont Ave) Near the mall, casino, racetrack, shopping, and many restaurants. Killens Pond State Park is a 10 min drive. Harrington Casino the Del. State Fair is 15 mins from us.

Nov 20 – 27

R2,236 ZAR per night

Home in Milton

4.83 out of 5 average rating, 215 reviews

Glennie's Places Scenic town close to beaches

A small historic home in the city of Milton, De. Milton offers small town charm which is minutes away from the beaches. This home has recent upgrades, renovations and new central air/heating. Enjoy the sunshine off of the back deck while preparing your BBQ. Take in a short walk downtown Milton to the city park which is a few minutes from the house along the Broadkill River. Check out some of the gift shops, eateries, The Milton Theatre, or a tour of the world renown Dogfish Head Brewery.

Sep 8 – 15

R2,291 ZAR per night

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!

Sep 9 – 16

R1,266 ZAR per night

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Oct 1 – 8

R2,722 ZAR per night

Guesthouse in Easton

4.99 out of 5 average rating, 545 reviews

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.

Nov 19 – 24

R2,802 ZAR per night

Home in Milford

4.99 out of 5 average rating, 111 reviews

Fully Renovated 1940s Cottage near everything!

Completely renovated in 2017, the home was originally built in 1946 by a returning WWII veteran who married the farmers daughter next door. The home features all new dual zone hvac, quartz countertops, marble thresholds, hand inlayed wood flooring, shiplap throughout, original crown molding, formal dining room featuring a handmaid 1800s barn-wood table, enclosed/screened in back porch, large smart TVs throughout, and a level 2 electric car charger is available by request.

Mar 13 – 20

R3,828 ZAR per night

Apartment in Frankford

4.98 out of 5 average rating, 123 reviews

Cozy Cottage Getaway

Enjoy this newly remolded 1 bedroom apartment tucked away on 2+ acres 3 miles from Bethany beach. Close to Rehobeth beach for outlet tax free shopping or Ocean City MD just 13 miles. You’ll be minutes away from lots of restaurants, stores, mini golf, arcade, night life etc. Property includes a 1/4 mile walking/running trail, fire pit and basket ball court. This is the perfect place to escape away from the busy Beach life but close enough to enjoy everything fully.

Oct 13 – 20

R2,914 ZAR per night

Apartment in Milton

4.96 out of 5 average rating, 132 reviews

Beachin' Inn Milton

Welcome to Beachin' Inn Milton! This cozy apartment located in the quaint, historical town of Milton, DE is the perfect getaway. Our apartment is light and airy with a beach theme. Enjoy the entire apartment to yourself with a keyless private entrance, full bath, washer/dryer, free Wifi and stocked assorted coffee pods. There is no stove/oven, however, we offer a microwave, toaster oven, Air Fryer and induction burner.There is private parking right out front.

Oct 8 – 15

R2,325 ZAR per night

Home in Milford

4.81 out of 5 average rating, 156 reviews

Poe Themed Home Close to Beaches and DE Turf

Looking for a unique stay in Delaware? Check out our Edgar Allan Poe themed house. 3 bedrooms and 1 full bath in an historic house built in the late 1800’s. In the heart of beautiful downtown Milford, you’ll be able to walk to coffee shops, restaurants and the historic Riverwalk. **THERE IS NOT A FULL KITCHEN IN THIS UNIT, just a very basic kitchenette. There is a microwave, keurig coffee maker, refrigerator, and toaster oven available for your convenience.

Feb 9 – 16

R2,766 ZAR per night

Guesthouse in Milton

4.97 out of 5 average rating, 149 reviews

The Book Nook - A Private Downtown Retreat

In the heart of downtown Milton, you will find a newly renovated guest cottage less than 10 miles to the beach! If you plan on staying local, simply park your car at the designated off-street parking space and travel by foot to the many shops, restaurants, and attractions offered in historic Milton. Whether you're walking the few short blocks to Dogfish Head Brewery or spending an evening at the theater, The Book Nook will serve as the perfect location!

May 8 – 15

R3,519 ZAR per night

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Popular amenities for Greenwood vacation rentals

Free parking on premises

Air conditioning

Stay near Greenwood's top sights

Cafe Tamburelli3 locals recommend

Amity Coffee3 locals recommend

Wilderlove3 locals recommend

Other great vacation rentals in Greenwood

Home in Milford

4.94 out of 5 average rating, 109 reviews

Sandcastle at the Bay/Beach Front Home- 3BR/2FB

May 25 – Jun 1

R5,067 ZAR per night

Home in Georgetown

4.85 out of 5 average rating, 107 reviews

Maplewood - Simply Comfortable, Dog Friendly

Sep 25 – Oct 2

R2,897 ZAR per night

Apartment in Milford

4.91 out of 5 average rating, 89 reviews

Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Sep 12 – 19

R1,917 ZAR per night

Apartment in Ellendale

4.94 out of 5 average rating, 53 reviews

Near Beaches and outlets.

Sep 10 – 17

R2,783 ZAR per night

Home in Greensboro

4.96 out of 5 average rating, 47 reviews

Cozy 2 bedroom home on wooded private lane

Mar 25 – Apr 1

R2,502 ZAR per night

Guest suite in Greenwood

4.86 out of 5 average rating, 98 reviews

Romantic Hideaway- jacuzzi, beach day!

Apr 11 – 18

R3,759 ZAR per night

Tiny home in Lincoln

5.0 out of 5 average rating, 6 reviews

Wild Nest Tiny House In Woods

Sep 28 – Oct 5

R2,002 ZAR per night

Apartment in Frederica

4.99 out of 5 average rating, 91 reviews

Entire 1-Bedroom apt. - Private entrance in home

Oct 21 – 28

R2,309 ZAR per night

Destinations to explore