Best Vacation Homes in Hampshire
425 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $227/Night
For 7 Nights US $1,588
570.49 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Pet Friendly
US $213/Night
For 7 Nights US $1,488
US $248/Night
For 7 Nights US $1,736
425 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $227/Night
For 7 Nights US $1,588
10763.91 ft²
6 Guests
1 Bedroom
2 Bathrooms
Family Friendly
House
- Pet Friendly
- Parking
- Air Conditioner
US $171/Night
For 7 Nights US $1,197
575 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $225/Night
For 7 Nights US $1,575
575 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $240/Night
For 7 Nights US $1,682
425 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $227/Night
For 7 Nights US $1,588
Hampshire Luxury Rentals
16 Guests
5 Bedrooms
3 Bathrooms
Pet Friendly
House
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $1,152/Night
For 7 Nights US $8,063
14 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Hot Tub
- Fireplace/Heating
- Air Conditioner
US $956/Night
For 7 Nights US $6,692
4 Guests
6 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $601/Night
For 7 Nights US $4,210
90 Guests
4 Bedrooms
2 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $521/Night
For 7 Nights US $3,644
1744 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $514/Night
For 7 Nights US $3,598
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $497/Night
For 7 Nights US $3,477
1744 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $494/Night
For 7 Nights US $3,458
2000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $420/Night
For 7 Nights US $2,937
Hampshire Pet Friendly Vacation Rentals
575 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $240/Night
For 7 Nights US $1,682
570.49 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- View
- Pet Friendly
US $213/Night
For 7 Nights US $1,488
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
US $115/Night
For 7 Nights US $808
575 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $219/Night
For 7 Nights US $1,536
566.18 ft²
22 Guests
7 Bedrooms
7 Bathrooms
Bed & Breakfast
- Oceanfront
- Fireplace/Heating
- Pool
US $163/Night
For 7 Nights US $1,140
4 Guests
3 Bedrooms
1 Bathroom
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $317/Night
For 7 Nights US $2,218
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $297/Night
For 7 Nights US $2,077
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $173/Night
For 7 Nights US $1,214
Hampshire Large Vacation Homes
7 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $241/Night
For 7 Nights US $1,688
1507 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $391/Night
For 7 Nights US $2,739
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Internet
US $582/Night
For 7 Nights US $4,071
1841 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $378/Night
For 7 Nights US $2,646
1507 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $429/Night
For 7 Nights US $3,004
1900 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
US $2,168/Night
For 7 Nights US $15,177
1420 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $652/Night
For 7 Nights US $4,563
1420 ft²
16 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
US $646/Night
For 7 Nights US $4,523
Why Choose Rent By Owner for your Hampshire 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 Hampshire
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit can enhance your experience, so consider planning your trip during the region’s most favorable seasons when the weather and local events align to create a memorable getaway.
Peak Season Highlights
Summer (June to August)
This destination experiences its peak season during the warm summer months, making it ideal for outdoor activities and enjoying the local scenery. Expect higher demand for vacation rentals as visitors flock here for the pleasant weather.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to November)
Autumn brings vibrant foliage and a festive atmosphere, attracting many travelers seeking the region's scenic beauty. Booking early ensures you secure comfortable accommodations during this popular season.
Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F
Off-Season Highlights
Winter (December to February)
During the colder months, fewer visitors explore the area, providing an excellent opportunity for peaceful stays. Enjoy more available lodging options at attractive rates in this quieter season.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Spring (March to May)
Before the summer rush, spring offers mild weather and blooming landscapes, making it a charming time for a visit when accommodations are generally more accessible and affordable.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Hampshire
How to Book Your Hampshire 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 Hampshire
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 outdoor seating areas such as patios or decks to relax and dine al fresco amidst the scenic surroundings.
- Take advantage of private or shared gardens, perfect for lounging or exploring the local flora.
- Make use of outdoor fire pits or fireplaces for cozy evenings under the stars.
- Benefit from well-maintained yards or lawns ideal for outdoor activities or picnics.
- Explore nearby hiking or walking trails accessible directly from your rental property.
- Utilize outdoor recreational equipment like bikes, kayaks, or paddleboards often available for rent or included.
- Experience the region's natural beauty with spacious outdoor spaces designed for leisure and relaxation.
Top Attractions Around Hampshire
What attractions are nearby?
Here, you can explore a variety of outdoor activities and local attractions that make this destination a perfect spot for a memorable getaway near Hampshire, Illinois, USA.
Family Activities
- Hampshire Community Park: Enjoy family picnics, playground fun, and outdoor activities in this popular local park that offers a relaxing escape for all ages.
- Stratford Square Mall: Discover a variety of shopping, dining, and entertainment options perfect for a family day out in the heart of the region.
- Local Nature Trails: Explore scenic walking and biking trails around here, ideal for nature-loving families seeking outdoor adventures close to your vacation rental.
- Community Events and Festivals: Participate in seasonal festivals and family-friendly events held regularly, offering engaging entertainment right here in the area.
Adult Activities
- Hampshire Area Trails: Explore scenic trails perfect for hiking and biking, offering a tranquil escape into nature.
- Local Wineries and Breweries: Discover the region's vibrant wine and craft beer scene with tastings and tours available nearby.
- Historic Downtown Hampshire: Stroll through charming shops, dine at local eateries, and enjoy the small-town atmosphere of this destination.
- Community Events and Festivals: Participate in seasonal festivals and outdoor markets that showcase the area's local culture and entertainment options.
Hampshire Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Check out community calendars to discover seasonal events that offer authentic experiences and a glimpse into the area's vibrant culture.
- Plan Outdoor Activities: Take advantage of the region's scenic parks or recreational areas to enjoy activities like hiking, biking, or picnicking, making your stay more memorable.
- Visit Nearby Attractions: Research popular local attractions to maximize your time and uncover hidden gems that showcase the unique charm of this destination.
- Make Use of Local Dining Options: Savor the region’s cuisine by exploring nearby eateries, ensuring you experience the flavors that define this part of Illinois.
Transportation Options
- Hampshire Transit Authority: Provides reliable local bus services that make exploring the area convenient for visitors staying in vacation rentals.
- Amtrak Station in nearby cities: Connects you to major cities across the region, offering a comfortable and scenic travel option from here.
- Car Rentals: Available at various locations within the area, giving you the flexibility to explore Hampshire and its surroundings at your own pace.
- Taxis and Rideshare Services: Easily accessible options for quick trips or airport transfers, ensuring seamless transportation during your stay here.
Local Customs Options
- Hampshire's Local Festivals: Participating in community festivals provides an authentic way to experience the area's rich cultural heritage and friendly local spirit.
- Traditional Amish Honoring: Respect for Amish customs, such as their farming practices and handcrafted goods, offers insight into this region’s unique historical influences.
- Seasonal Agricultural Events: Engaging in harvest celebrations and farmers' markets reflects the region's dedication to sustainable farming and local produce.
- Respect for Nature and Outdoor Customs: The community values outdoor activities like hiking and picnicking, which are deeply rooted in appreciating the area's natural beauty.
Frequently Asked Questions About Hampshire?
1. What are the top vacation rentals in Hampshire?
There are a lot of options in Hampshire. If you plan on staying in the Hampshire area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Hampshire:
- 124 Lofts - Downtown Dundee - Walk to Dining
- Sinclair Suites
- 124 Lofts - Downtown Dundee - Walk to Dining
- The River House/Stunning Riverfront/Scenic Views/Water Sports/Steps to Marina
- Kildahl House - Boutique Farmhouse Suite #3
- Kildahl House - Boutique Farmhouse Suite #4
- 124 Lofts - Downtown Dundee - Walk to Dining
- 124 Lofts - Downtown Dundee - Walk to Dining
- Kildahl House - Boutique Farmhouse Suite #2
- Kildahl House - Boutique Farmhouse Suite #3
2. How many vacation rentals have private pools in Hampshire?
There are 9 vacation rentals with private pools near Hampshire. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Hampshire are best for families?
If you are looking for a family-friendly vacation home in Hampshire, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Hampshire:
4. How many Rentbyowner vacation rentals are available in Hampshire?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 173 in the Hampshire 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 Hampshire.
5. What is the cancellation policy for vacation rentals in Hampshire, Illinois?
Cancellation policies can vary depending on the individual property owner. To ensure you have the most accurate information, please review the specific listing details or contact the owner directly before booking.
6. Are there any additional fees I should expect when booking a vacation rental in the area?
Additional fees such as cleaning fees, service charges, or local taxes may apply. These will be clearly outlined in the listing, so it's advisable to review all fee details prior to confirming your reservation.
7. How do I confirm the availability of a vacation rental in this destination?
Availability is typically displayed on the listing page. For real-time confirmation, it’s best to reach out directly to the property owner or manager through the platform's messaging system.
8. What amenities are usually included with vacation rentals in this part of Illinois?
Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. For detailed information about what is offered, check the specific listing or contact the owner directly.
9. Is it possible to modify or cancel my reservation if my travel plans change?
Reservation modification and cancellation options depend on the property's policies. Be sure to read the cancellation and modification terms listed on the property page or communicate directly with the host for assistance.
Hampshire Top Rated Vacation Rentals
US $123/Night
For 7 Nights US $858
US $126/Night
For 7 Nights US $879
US $139/Night
For 7 Nights US $973
446.7 ft²
14 Bathrooms
Ocean View
Hotel
- Private Pool
- Oceanfront
- Hot Tub
US $132/Night
For 7 Nights US $924
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $94/Night
For 7 Nights US $660
386.3 ft²
7 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $210/Night
For 7 Nights US $1,472
US $115/Night
For 7 Nights US $805
14 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $140/Night
For 7 Nights US $980
