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Holiday rentals in Greenwood

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Top-rated holiday rentals in Greenwood

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Tiny home in Cambridge

4.89 out of 5 average rating, 497 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!

31 Aug – 7 Sep

$119 SGD per night

Guest favourite

Flat in Dewey Beach

4.95 out of 5 average rating, 133 reviews

DeweyBeach 1 BR + sleeper sofa. Walk to the beach!

Enjoy all of Dewey Beach at this delightful 1 BR, ground floor, apartment on the north side of town. 1.5 blocks to the beach, and 3 blocks to the start of restaurants and music venues. Quiet, relaxing location on a side street. Perfect for a small family or group of 4 friends! Custom self check-in keypad code for Private Entry sent upon booking. Professionally cleaned + bed made before your stay. 4 beach chairs, 1 on-property parking spot + 1 free Street Parking Passes provided at no charge!

23–30 Dec

$121 SGD per night

Guest favourite

Flat in Greenwood

4.97 out of 5 average rating, 477 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)

19–26 Sep

$112 SGD per night

Guest favourite

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.

2–9 May

$155 SGD per night

Guest favourite

Flat 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!

11–18 Sep

$89 SGD per night

Guest favourite

Guest house in Easton

4.99 out of 5 average rating, 543 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.

10–15 Nov

$196 SGD per night

Guest favourite

Home in Greensboro

4.96 out of 5 average rating, 46 reviews

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

10–17 Oct

$175 SGD per night

Guest favourite

Flat 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.

2–9 May

$162 SGD per night

Guest favourite

Home in Georgetown

4.85 out of 5 average rating, 106 reviews

Maplewood - Simply Comfortable, Dog Friendly

Have fun with the whole family at this stylish place in the center of it all. Near the beach, away from the crowds. Local attractions: Sandhill Fields - .5 miles Sports at the Beach - 1 mile Dogfish Head Brewery - 5 miles Lewes Beach -8 Cape May Lewes Ferry Terminal Cape Henlopen State Park Tanger Outlets - 12.4 miles - 13.9 miles And lots of other tax free shopping. Rehoboth Beach Boardwalk - 17.5 miles Dover Downs - 39.1 miles Many other attractions nearby.

27 Aug – 3 Sep

$202 SGD 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.

1–8 Oct

$193 SGD per night

Guest favourite

Guest house in Milton

4.97 out of 5 average rating, 148 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!

6–13 May

$246 SGD per night

Guest favourite

Tiny home in Cambridge

4.99 out of 5 average rating, 155 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.

12–19 Sep

$146 SGD per night

Holiday rentals for every style

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Popular amenities for Greenwood holiday 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 holiday rentals in Greenwood

Guest favourite

Tiny home in Lincoln

5.0 out of 5 average rating, 6 reviews

Wild Nest Tiny House In Woods

29 Aug – 5 Sep

$148 SGD per night

Guest favourite

Guest suite in Greenwood

4.86 out of 5 average rating, 98 reviews

Romantic Hideaway- jacuzzi, beach day!

25 Feb – 4 Mar

$266 SGD per night

Guest favourite

Flat in Frederica

4.99 out of 5 average rating, 91 reviews

Entire 1-Bedroom apt. - Private entrance in home

28 Oct – 4 Nov

$166 SGD per night

Flat in Milford

4.91 out of 5 average rating, 89 reviews

Luxury 2 bedroom Apt. Near DE Turf & Beaches!

24–31 Aug

$208 SGD per night

Guest favourite

Cottage in Bridgeville

5.0 out of 5 average rating, 32 reviews

Cozy home on the beautiful Delaware Countryside.

13–20 Jul

$739 SGD per night

Guest favourite

Serviced apartment in Kent County

4.89 out of 5 average rating, 76 reviews

The Country Cottage

22–29 Mar

$135 SGD per night

Guest favourite

Tiny home in Milford

4.9 out of 5 average rating, 51 reviews

Peaceful Possibilities - Tiny Home with Farm View

22–29 Oct

$124 SGD per night

Guest favourite

Home in Greenwood

4.84 out of 5 average rating, 25 reviews

Lots of space in this country home & property

5–12 Oct

$464 SGD per night

Destinations to explore