Best Vacation Homes in Greenwood
Cottage
10.0(130 Reviews)
2 Bedrooms
1 Bath
3 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
AU $222/Night
7 Nights - AU $1,552
House
10.0(3 Reviews)
3 Bedrooms
3 Baths
5 Guests
1302.43 ft²
- Parking
Internet
Child Friendly
Security/Safety
AU $309/Night
7 Nights - AU $2,163
Bed & Breakfast
10.0(125 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
Kitchen
AU $311/Night
7 Nights - AU $2,178
House
10.0(91 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
Air Conditioner- Internet
AU $270/Night
7 Nights - AU $1,891
Bed & Breakfast
9.7(49 Reviews)
6 Bedrooms
5 Baths
12 Guests
279.86 ft²
- Parking
View- Air Conditioner
- Internet
AU $298/Night
7 Nights - AU $2,084
Cabin
10.0(37 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
AU $249/Night
7 Nights - AU $1,744
House
10.0(36 Reviews)
2 Bedrooms
1 Bath
5 Guests
480 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $316/Night
7 Nights - AU $2,214
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
398 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
AU $321/Night
7 Nights - AU $2,244
Greenwood Luxury Rentals
House
9.6(13 Reviews)
4 Bedrooms
2 Baths
12 Guests
Private Pool
Hot Tub- Parking
Pool
AU $1,231/Night
7 Nights - AU $8,617
House
8.6(7 Reviews)
3 Bedrooms
3 Baths
12 Guests
1991.32 ft²
- Parking
- Balcony/Terrace
- Child Friendly
Sports/Activities
AU $790/Night
7 Nights - AU $5,528
Apartment
10.0(1 Review)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $599/Night
7 Nights - AU $4,193
House
9.8(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $582/Night
7 Nights - AU $4,073
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $517/Night
7 Nights - AU $3,618
House
7.4(3 Reviews)
3 Bedrooms
2 Baths
12 Guests
1989 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
AU $504/Night
7 Nights - AU $3,524
House
10.0(4 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $469/Night
7 Nights - AU $3,281
House
10.0(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $441/Night
7 Nights - AU $3,085
Greenwood Pet Friendly Vacation Rentals
Cabin
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
AU $392/Night
7 Nights - AU $2,740
House
1 Bedroom
3 Baths
6 Guests
161.46 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
AU $362/Night
7 Nights - AU $2,531
Condo
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Kitchen
AU $345/Night
7 Nights - AU $2,413
Hotel
8.7(157 Reviews)
1 Bath
301.39 ft²
- Private Pool
- Oceanfront
- Breakfast
- Parking
AU $177/Night
7 Nights - AU $1,238
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Air Conditioner
- Internet
- Pet Friendly
AU $364/Night
7 Nights - AU $2,549
House
9.6(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $441/Night
7 Nights - AU $3,088
Condo
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Pet Friendly
AU $354/Night
7 Nights - AU $2,481
House
4 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
AU $600/Night
7 Nights - AU $4,198
Greenwood Large Vacation Homes
House
8.4(9 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Child Friendly
- Security/Safety
AU $482/Night
7 Nights - AU $3,374
House
7.6(8 Reviews)
3 Bedrooms
2 Baths
12 Guests
1989 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $345/Night
7 Nights - AU $2,413
House
9.8(25 Reviews)
9 Bedrooms
7 Baths
15 Guests
6800 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
AU $2,018/Night
7 Nights - AU $14,127
Why Choose Rent By Owner for your Greenwood Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Greenwood
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this destination allows you to enjoy the region's climate and local ambiance, ensuring your stay in Greenwood aligns perfectly with your vacation plans and preferences.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you'll enjoy warm weather ideal for outdoor activities and exploring local attractions in the region. This is the busiest time for vacation rentals, so advanced booking is recommended to secure your perfect stay.
Average Temperature Daytime: 85°F - Nighttime: 65°F
Fall (September to November)
Autumn brings pleasant weather and vibrant foliage, making it a popular season to visit the area. The comfortable temperatures are perfect for sightseeing and enjoying the natural landscape, attracting many visitors during this time.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Off-Season Highlights
Winter (December to February)
In the winter months, the region sees fewer visitors, providing a quieter experience for those seeking tranquility and lower rates on vacation rentals. Mild temperatures make it suitable for cozy stays and off-season exploration.
Average Temperature Daytime: 45°F - Nighttime: 30°F
Spring (March to May)
Early spring offers a peaceful retreat before the summer crowds arrive, with blooming landscapes adding charm to your visit. Booking this period allows for an affordable and relaxed getaway in this destination.
Average Temperature Daytime: 60°F - Nighttime: 40°F
Weekly Weather Forecast for Greenwood
How to Book Your Greenwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy private outdoor seating areas perfect for relaxing and dining al fresco.
- Take advantage of spacious yards ideal for outdoor games and activities.
- Make use of a barbecue grill to host enjoyable cookouts with family and friends.
- Relax by a swimming pool or hot tub, if available, to refresh during warm days.
- Benefit from well-maintained gardens or landscaped spaces that enhance the outdoor experience.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
- Access nearby walking trails or nature paths common in this region for outdoor exploration.
Top Attractions Around Greenwood
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities and local attractions that showcase the best of Greenwood’s nearby countryside and community events, making it an ideal destination for a relaxing and engaging getaway.
Family Activities
- Greenwood Nature Trail: Embark on a family-friendly hike along this scenic trail to enjoy the area's lush landscapes and local wildlife.
- Deep Branch Park: Spend quality time at this community park, perfect for picnics, playground fun, and outdoor games with your loved ones.
- Greenwood Historical Museum: Discover the region’s rich history through engaging exhibits that offer educational entertainment for children and adults alike.
- Local Farm Tours: Experience the area’s agricultural roots by visiting nearby farms, where your family can learn about farming practices and interact with farm animals.
Adult Activities
- Gunpowder State Park: Immerse yourself in nature by exploring scenic trails, picnicking areas, and outdoor activities within this popular park nearby.
- Rehoboth Bay Water Activities: Enjoy kayaking, paddleboarding, or fishing on the tranquil waters of Rehoboth Bay, offering a relaxing escape close to your stay.
- Greenwood Historical Society Museum: Discover local history and culture through engaging exhibits that provide insight into the area's rich heritage.
- Golf at The Rookery Golf Course: Tee off at this well-maintained golf course, ideal for adults seeking leisure and scenic views just a short drive away.
Other Places to Stay in Greenwood, DE
Farmington
Greenwood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Seasons: Research the area's seasonal trends to optimize your visit and enjoy outdoor activities when the weather is at its best.
- Explore Nearby Nature Spots: Take advantage of the region’s natural beauty by visiting nearby parks and trails during your stay in Greenwood.
- Discover Local Events and Festivals: Check the local calendar for events that will enrich your experience and give you a taste of this destination's community spirit.
- Choose Comfortable, Well-Reviewed Vacation Rentals: Select accommodations with positive reviews to ensure a relaxing and memorable visit here, making the most of your time in this region.
Transportation Options
- Greenwood Transit Bus Service: This local bus system offers convenient connections within the area, making it easy to explore nearby attractions and amenities.
- Rental Cars: Numerous rental agencies in the region provide flexible transportation options for your stay, allowing you to navigate Greenwood and beyond at your own pace.
- Taxi and Rideshare Services: Taxis and rideshare companies operate here, offering quick and reliable transport for short trips around town or to neighboring destinations.
- Local Taxi Services: Independent taxi providers serve the area, providing a dependable way to reach your vacation rental or explore the local surroundings comfortably.
Local Customs Options
- Greetings and Hospitality: Visitors are warmly welcomed here, with locals valuing politeness and friendly interactions to foster a sense of community in the area.
- Festivals and Celebrations: Participating in local festivals that celebrate seasonal harvests and regional heritage offers an authentic experience of the region's customs.
- Respect for Nature: The community emphasizes environmental stewardship, encouraging visitors to enjoy outdoor activities responsibly and preserve the area's natural beauty.
- Dining Etiquette: Sharing meals at family-style gatherings is common, where good manners and appreciation for regional cuisine play a significant role in social interactions here.
Frequently Asked Questions About Greenwood?
1. What are the top vacation rentals in Greenwood?
There are a lot of options in Greenwood. If you plan on staying in the Greenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greenwood:
- Grandma's Cottage Milford Delaware
- The Towers Bed & Breakfast
- Swartzentruber Cottage close to DE Turf & Beaches, also for traveling nurses!
- Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
- Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
- Luxury Treehouse with Large Deck
- Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
- Wonderful 3-bedroom bungalow only 10 minutes from Delaware Turf Complex.
- Cozy condo, 30 minutes away from the beach, outlets and boardwalk.
- Cozy Unit in Milford, Delaware -Close to DE Turf
2. How many vacation rentals have private pools in Greenwood?
There are 4 vacation rentals with private pools near Greenwood. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Greenwood are best for families?
If you are looking for a family-friendly vacation home in Greenwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenwood:
4. How many Rentbyowner vacation rentals are available in Greenwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 64 in the Greenwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greenwood.
5. How do I find the cancellation policy for my chosen vacation rental in Greenwood, Delaware?
You can review the specific cancellation policy by checking the listing details on the booking platform. If you have any questions or need clarification, it’s best to contact the property owner directly before confirming your reservation.
6. What amenities should I expect when booking a vacation rental in this area?
The amenities vary by property, so it’s important to read the listing carefully. Common features include Wi-Fi, parking, and kitchen facilities. For additional amenities, reach out to the host for further details.
7. Are there any specific check-in and check-out times I should be aware of in Greenwood, Delaware?
Check-in and check-out times are typically listed on the property page. These times can differ between rentals, so reviewing the details or speaking with the property owner ensures a smooth arrival and departure.
8. What is the process if I need to modify or cancel my reservation in the region?
Modification and cancellation policies are outlined in the listing. For changes or cancellations, contact the property owner promptly through the platform to ensure proper handling according to their guidelines.
9. How do I ensure my stay complies with local regulations in this destination?
It’s advisable to verify any regional rules or restrictions with the property owner prior to booking. They can provide guidance on local regulations that might affect your stay.
Greenwood Top Rated Vacation Rentals
Hotel
9.4(128 Reviews)
1 Bath
355.21 ft²
- Private Pool
- Parking
- Pool
- Air Conditioner
AU $183/Night
7 Nights - AU $1,280
Hotel
9.0(1010 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
AU $163/Night
7 Nights - AU $1,141
AU $231/Night
7 Nights - AU $1,618
AU $166/Night
7 Nights - AU $1,165
Hotel
8.8(762 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
AU $142/Night
7 Nights - AU $991
Hotel
8.8(132 Reviews)
8 Baths
330.99 ft²
- Oceanfront
- Breakfast
- Parking
- Pool
AU $263/Night
7 Nights - AU $1,839
Hotel
8.4(288 Reviews)
8 Baths
298.7 ft²
- Oceanfront
- Breakfast
EV Charge Station- Parking
AU $229/Night
7 Nights - AU $1,605
Hotel
7.8(225 Reviews)
1 Bath
319.33 ft²
- Private Pool
- Parking
- Pool
- Internet
AU $383/Night
7 Nights - AU $2,684
