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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!

Sep 23 – 30

G$17,547 GYD 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 24 – Dec 1

G$17,136 GYD 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.

Dec 2 – 9

G$23,877 GYD 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 9 – 16

G$24,426 GYD 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!

Oct 27 – Nov 3

G$14,990 GYD 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.

Sep 13 – 20

G$29,096 GYD 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.

Mar 22 – 27

G$29,956 GYD 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 15 – 22

G$40,884 GYD 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.

Sep 13 – 20

G$24,843 GYD 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.

Aug 31 – Sep 7

G$29,556 GYD 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

G$37,600 GYD per night

Tiny home in Cambridge

4.99 out of 5 average rating, 156 reviews

Blackwater Refuge House on The Farm, water access

The Little House on The Farm is located on a beautiful family farm in rural Dorchester County! Located just 1.5 miles from the Blackwater Wildlife Refuge and Harriet Tubman National Park, This space is quaint,yet provides all the basics for a cozy welcoming getaway! Bring your bikes and cycle to the refuge and kayak in the Blackwater River. Kitchen is fully stocked for cooking. Coffee, tea and basic condiments and all linens and towels are provided.

Aug 31 – Sep 7

G$22,441 GYD 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

Apartment in Dover

4.9 out of 5 average rating, 156 reviews

Apartment A Woodbrook Cottage 5G WiFi

Feb 6 – 13

G$22,266 GYD per night

Apartment in Ellendale

4.94 out of 5 average rating, 53 reviews

Near Beaches and outlets.

Sep 5 – 12

G$29,730 GYD per night

Home in Greensboro

4.96 out of 5 average rating, 47 reviews

Cozy 2 bedroom home on wooded private lane

Apr 14 – 21

G$26,775 GYD per night

Guest suite in Greenwood

4.86 out of 5 average rating, 98 reviews

Romantic Hideaway- jacuzzi, beach day!

Oct 12 – 19

G$40,902 GYD per night

Tiny home in Lincoln

5.0 out of 5 average rating, 6 reviews

Wild Nest Tiny House In Woods

Jun 28 – Jul 5

G$23,256 GYD per night

Apartment in Milford

4.85 out of 5 average rating, 40 reviews

2 room studio Apartment Downtown Milford

Mar 4 – 11

G$19,665 GYD per night

Tiny home in Milford

4.9 out of 5 average rating, 51 reviews

Peaceful Possibilities - Tiny Home with Farm View

Oct 22 – 29

G$18,863 GYD per night

Apartment in Frederica

4.99 out of 5 average rating, 91 reviews

Entire 1-Bedroom apt. - Private entrance in home

Nov 27 – Dec 4

G$25,038 GYD per night

Destinations to explore