Best Vacation Homes in Gregory
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $182/Night
For 7 Nights US $1,272
US $110/Night
For 7 Nights US $767
US $159/Night
For 7 Nights US $1,110
8 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $301/Night
For 7 Nights US $2,106
301.39 ft²
8 Guests
5 Bedrooms
1 Bathroom
House
- Balcony/Terrace
- Pet Friendly
- Parking
US $120/Night
For 7 Nights US $840
6 Guests
2 Bedrooms
1 Bathroom
Ocean View
RV Rental
- Oceanfront
- Fireplace/Heating
- Ocean View
US $187/Night
For 7 Nights US $1,311
6 Guests
1 Bedroom
1 Bathroom
Ocean View
Cabin
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $316/Night
For 7 Nights US $2,215
2 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
US $239/Night
For 7 Nights US $1,671
Gregory Luxury Rentals
17 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $580/Night
For 7 Nights US $4,057
15 Guests
5 Bedrooms
3 Bathrooms
Ocean View
Cabin
- Hot Tub
- Fireplace/Heating
- Ocean View
US $552/Night
For 7 Nights US $3,863
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $536/Night
For 7 Nights US $3,750
2109.73 ft²
10 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $480/Night
For 7 Nights US $3,360
4 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Kitchen
US $476/Night
For 7 Nights US $3,334
16 Guests
7 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $462/Night
For 7 Nights US $3,234
1700 ft²
12 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $450/Night
For 7 Nights US $3,148
1560.77 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Parking
- Internet
US $430/Night
For 7 Nights US $3,010
Gregory Pet Friendly Vacation Rentals
3600 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $199/Night
For 7 Nights US $1,395
288.47 ft²
14 Guests
43 Bedrooms
5 Bathrooms
Free Cancellation
Cabin
- Fireplace/Heating
- Pet Friendly
- Parking
US $132/Night
For 7 Nights US $926
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Pool
- Breakfast
US $94/Night
For 7 Nights US $658
1200 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $173/Night
For 7 Nights US $1,210
432.1 ft²
7 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $136/Night
For 7 Nights US $950
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $283/Night
For 7 Nights US $1,978
2115 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $427/Night
For 7 Nights US $2,987
6 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $342/Night
For 7 Nights US $2,396
Gregory Large Vacation Homes
16 Guests
6 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $378/Night
For 7 Nights US $2,645
1500 ft²
9 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- View
US $154/Night
For 7 Nights US $1,075
12 Guests
4 Bedrooms
3 Bathrooms
Group Friendly
Cabin
- Fireplace/Heating
- Internet
- Child Friendly
US $391/Night
For 7 Nights US $2,739
15 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $425/Night
For 7 Nights US $2,975
23 Guests
8 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $180/Night
For 7 Nights US $1,260
19 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $506/Night
For 7 Nights US $3,541
10 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $250/Night
For 7 Nights US $1,750
1200 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Kitchen
- Air Conditioner
- Internet
US $298/Night
For 7 Nights US $2,086
Why Choose Rent By Owner for your Gregory 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 Gregory
When should you plan your Vacation Rentals stay?
Timing your visit to Gregory allows you to enjoy this destination’s unique charm at its best, so consider planning your trip during the seasons when the region offers ideal weather and local events, ensuring a memorable and comfortable stay in this area.
Peak Season Highlights
Summer (June to August)
During the summer months, this area experiences its warmest weather, making it ideal for outdoor activities and exploring the natural beauty. Booking a vacation rental now ensures you enjoy the well-loved peak season amenities and long daylight hours.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to October)
Autumn brings vibrant foliage and mild temperatures, attracting visitors seeking scenic views and crisp air. Securing your stay during this popular season offers a tranquil escape amid colorful landscapes.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Winter (December to February)
The winter months are quieter in this region, with colder weather and fewer visitors. This is an excellent time to find cozy vacation rentals and enjoy peaceful surroundings at a more relaxed pace.
Average Temperature Daytime: 20-35°F - Nighttime: 0-15°F
Spring (March to May)
As nature begins to awaken, spring offers milder weather and fewer crowds. Planning ahead can help you find exceptional vacation rentals to experience the area's renewal and tranquility.
Average Temperature Daytime: 45-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Gregory
How to Book Your Gregory 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.
Explore and book the perfect rental in Gregory
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 spacious outdoor seating areas perfect for relaxing evenings under the stars.
- Take advantage of private or shared fire pits to gather around and share stories with friends or family.
- Make the most of well-maintained picnic areas equipped with tables for outdoor dining in the region’s scenic surroundings.
- Explore nearby trails and pathways suitable for hiking, biking, or leisurely walks amidst the area's natural beauty.
- Benefit from access to outdoor sports facilities such as volleyball courts or tennis courts, ideal for active guests.
- Relax in a hot tub or outdoor soaking pool that offers a soothing experience while enjoying the fresh air here in the region.
- Attend outdoor events or cultural festivals often hosted in the vicinity, making your stay even more memorable.
Top Attractions Around Gregory
What attractions are nearby?
Within this region, you can enjoy a variety of outdoor activities and local attractions that showcase the natural beauty and charm of South Dakota, making your stay here both relaxing and adventurous.
Family Activities
- Custer State Park South Dakota: Explore the scenic beauty and wildlife of this popular park, perfect for family picnics and nature hikes just a short drive from Gregory.
- Black Hills Playhouse South Dakota: Enjoy family-friendly outdoor theater performances in a beautiful setting that offers entertainment for all ages in the region.
- South Dakota Air and Space Museum: Discover fascinating exhibits and interactive displays that bring aviation history to life for curious minds here in the area.
- Badlands National Park South Dakota: Experience breathtaking landscapes and learn about the unique geology of this iconic national park, ideal for family adventures in the region.
Adult Activities
- Golfing at Gregory Golf Course: Enjoy a relaxing day on the lush fairways and challenging holes of this local golf course, perfect for both beginners and seasoned players seeking outdoor recreation.
- Hiking and Nature Walks: Explore scenic trails and immerse yourself in the region’s natural beauty through peaceful hikes around nearby parks and nature preserves.
- Fishing Opportunities: Cast your line in local lakes and streams known for their abundant fish populations, offering a tranquil escape for anglers staying in nearby vacation rentals.
- Historic Site Visits: Discover the area's rich history by visiting local landmarks and museums that showcase the heritage of the region, providing educational insights during your stay.
Other Places to Stay in Gregory, SD
Avera Gregory Hospital
Dallas
Gregory Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Check the regional calendar to participate in unique community events that showcase the area's culture and history during your stay.
- Plan Outdoor Activities: Take advantage of the region's natural beauty by scheduling outdoor adventures such as hiking or fishing, ensuring you experience the best of this destination's landscape.
- Book Strategic Accommodation: Secure your stay early with dependable vacation rentals to enjoy a comfortable and convenient base from which to explore the local attractions.
- Discover Nearby Dining Options: Sample authentic regional cuisine by researching popular local eateries and hidden gems within easy reach of your rental home here.
Transportation Options
- Driving your own vehicle: The most flexible way to explore this destination is by car, giving you the freedom to visit nearby attractions at your own pace.
- Regional bus services: Scheduled buses connect the area with larger cities, providing a convenient and affordable transportation option during your stay.
- Rental cars: Renting a car locally allows you to comfortably navigate the region and access remote or less accessible spots around here.
- Taxi and ride-sharing services: Taxis and ride-sharing options are available for quick, direct trips within the area, making it easy to get around without worries.
Local Customs Options
- South Dakota Hospitality Norms: Visitors often notice the friendly greeting and welcoming attitude of locals, reflecting the region's strong sense of community and openness.
- Traditional Farming Practices: Many here uphold longstanding agricultural customs, demonstrating their respect for the land and sustainable farming methods.
- Local Festivals and Events: Participating in regional celebrations is common, showcasing the area's pride in its heritage through music, food, and communal gatherings.
- Respect for Nature: Preservation of natural surroundings is valued, with residents and visitors alike practicing responsible recreation when exploring the outdoor scenery here.
Frequently Asked Questions About Gregory?
1. What are the top vacation rentals in Gregory?
There are a lot of options in Gregory. If you plan on staying in the Gregory area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Gregory:
- Log Cabin located minutes from Missouri River, airport, I-90 and downtown.
- Green Cedar Lodging - your play and stay destination.
- Perfect lodging for fishermen, hunters and family gatherings! Sleeping for 12.
- Sportsman's cabin near the Missouri River
- Comfortable cottage.
- Family-friendly, quiet and peaceful acreage minutes from the Missouri River.
- Cozy Little Getaway, Winner, SD
- Modern & luxurious 2-bedroom apartment with WiFi, AC on Main Street in Platte.
- Dakota Prairie Lodge & Resort
- Boar's Tusk Lodge
2. How many vacation rentals have private pools in Gregory?
There are 3 vacation rentals with private pools near Gregory. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Gregory are best for families?
If you are looking for a family-friendly vacation home in Gregory, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Gregory:
4. How many Rentbyowner vacation rentals are available in Gregory?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 79 in the Gregory 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 Gregory.
5. What is the cancellation policy for vacation rentals in Gregory, South Dakota?
Cancellation policies vary by property. To understand the specific terms and potential fees, review the listing details or contact the property owner directly before confirming your booking.
6. Are there any additional fees I should be aware of when booking a vacation rental in this region?
Additional fees such as cleaning, security deposits, or service charges are often outlined in the listing. Be sure to check the details on the property page or reach out to the host for clarifications.
7. How do I ensure my reservation in Gregory, South Dakota, is secure?
Reservations made through trusted platforms typically include secure payment options and verification processes. Always book through official listings and confirm with the host to ensure your reservation's safety.
8. What amenities are commonly available in vacation rentals around here?
Most vacation rentals in the area offer amenities like Wi-Fi, kitchen facilities, and parking. For specific features, review the property description carefully or contact the owner directly.
9. Is it possible to modify or cancel my booking if my plans change?
Modifications and cancellations depend on the individual property’s policies. Read the cancellation and modification terms listed for each rental and communicate directly with the host if needed.
Gregory Top Rated Vacation Rentals
US $131/Night
For 7 Nights US $920
US $124/Night
For 7 Nights US $867
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $116/Night
For 7 Nights US $809
267.56 ft²
14 Bathrooms
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Fireplace/Heating
US $155/Night
For 7 Nights US $1,085
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $85/Night
For 7 Nights US $592
US $79/Night
For 7 Nights US $550
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $94/Night
For 7 Nights US $657
329.07 ft²
11 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $145/Night
For 7 Nights US $1,017
