Hillandale pickleball Stays, Resort Rentals, & Homes
House
- College Park
- ·
- Silver Spring
- 2.00 mi to center
10.0Exceptional
(22 Reviews)
1 Bedroom
1 Bath
3 Guests
850 ft²
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $141/Night
7 Nights - US $985
Apartment
- College Park
- ·
- Calverton
- 0.31 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
215.28 ft²
- Parking
View- Air Conditioner
Internet
US $80/Night
7 Nights - US $561
House
- College Park
- ·
- Calverton
- 0.42 mi to center
1 Bedroom
1 Bath
- Parking
- Internet
Child Friendly
Laundry
US $396/Night
7 Nights - US $2,769
![Unique Tiny House Studio [With Chickens] Near I-95, FDA, DC, VA](https://imgservice.pickletrip.com/640x287/unique-tiny-house-us-silver-spring-ha-3213262734-0.jpg)
House
- College Park
- ·
- Silver Spring
- 2.53 mi to center
10.0Exceptional
(9 Reviews)
1 Bedroom
1 Bath
2 Guests
1300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $137/Night
7 Nights - US $957
Apartment
- College Park
- ·
- Silver Spring
- 1.94 mi to center
9.7Exceptional
(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $170/Night
7 Nights - US $1,191
Apartment
- College Park
- ·
- Silver Spring
- 0.99 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $217/Night
7 Nights - US $1,516
House
- College Park
- ·
- Beltsville
- 2.45 mi to center
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
5 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $88/Night
7 Nights - US $614
Apartment
- College Park
- ·
- Calverton
- 0.27 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $100/Night
7 Nights - US $700
Apartment
- College Park
- ·
- Takoma Park
- 0.76 mi to center
9.8Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $231/Night
7 Nights - US $1,614
Luxury Places to Stay in Hillandale
Over 187+ Luxury Places to Stay in or Near Hillandale
House
- College Park
- ·
- Adelphi
- 0.58 mi to center
6.8Good
(5 Reviews)
6 Bedrooms
3 Baths
16 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $1,061/Night
7 Nights - US $7,424
House
- College Park
- ·
- White Oak
- 0.27 mi to center
5 Bedrooms
4 Baths
15 Guests
2497.23 ft²
- Parking
- Balcony/Terrace
- Internet
Pet Friendly
US $861/Night
7 Nights - US $6,029
House
- College Park
- ·
- White Oak
- 0.27 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
15 Guests
2500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $841/Night
7 Nights - US $5,885
House
- College Park
- ·
- White Oak
- 0.22 mi to center
5.0Average
(2 Reviews)
1 Bedroom
5 Baths
20 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $768/Night
7 Nights - US $5,378
Villa
- College Park
- ·
- White Oak
- 0.27 mi to center
5 Bedrooms
4 Baths
16 Guests
2798.62 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $766/Night
7 Nights - US $5,365
House
- College Park
- ·
- White Oak
- 0.47 mi to center
8.8Fabulous
(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
3060 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $729/Night
7 Nights - US $5,106
House
- Maryland
- ·
- College Park
- 1.79 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $636/Night
7 Nights - US $4,449
House
- College Park
- ·
- Langley Park
- 0.79 mi to center
9.2Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $574/Night
7 Nights - US $4,021
House
- College Park
- ·
- Silver Spring
- 1.84 mi to center
9.4Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Parking
Ocean View- Balcony/Terrace
- View
US $568/Night
7 Nights - US $3,979
Top-Rated Villas with a Pool in Hillandale
Over 17+ Top-Rated Private Villas with a Pool in or Near Hillandale
Other
- Maryland
- ·
- College Park
- 3.07 mi to center
10.0Exceptional
(16 Reviews)
16 Bedrooms
10 Baths
47 Guests
844.2 ft²
Oceanfront- Hot Tub
EV Charge Station- Parking
US $316/Night
7 Nights - US $2,214
Hotel
- College Park
- ·
- Calverton
- 0.50 mi to center
8.8Fabulous
(615 Reviews)
1 Bath
Breakfast- Parking
Pool- Kitchen
US $192/Night
7 Nights - US $1,345
Hotel
- College Park
- ·
- Calverton
- 0.88 mi to center
8.6Fabulous
(1011 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $115/Night
7 Nights - US $804
Hotel
- College Park
- ·
- Hillandale
- 0.61 mi to center
8.6Fabulous
(362 Reviews)
1 Bath
301.39 ft²
Private Pool- Oceanfront
- Breakfast
- EV Charge Station
US $144/Night
7 Nights - US $1,011
Hotel
- Maryland
- ·
- College Park
- 2.83 mi to center
8.4Excellent
(1564 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $163/Night
7 Nights - US $1,139
Hotel
- Maryland
- ·
- College Park
- 1.32 mi to center
8.4Excellent
(1014 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $127/Night
7 Nights - US $886
Hotel
- Maryland
- ·
- College Park
- 1.33 mi to center
7.9Very Good
(433 Reviews)
8 Baths
300.31 ft²
- Breakfast
- Parking
- Pool
- Air Conditioner
US $138/Night
7 Nights - US $963
Hotel
- Maryland
- ·
- College Park
- 2.80 mi to center
7.6Very Good
(487 Reviews)
9 Baths
301.39 ft²
- Private Pool
- Oceanfront
- EV Charge Station
- Parking
US $114/Night
7 Nights - US $797
Hotel
- College Park
- ·
- Calverton
- 0.87 mi to center
7.6Very Good
(299 Reviews)
1 Bath
355.21 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $118/Night
7 Nights - US $827
Pet-Friendly Villas in Hillandale
Over 66+ Pet-Friendly Private Villas in or Near Hillandale
House
- College Park
- ·
- Takoma Park
- 0.62 mi to center
8.4Excellent
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $189/Night
7 Nights - US $1,324
Apartment
- College Park
- ·
- Takoma Park
- 0.62 mi to center
9.4Exceptional
(7 Reviews)
1 Bedroom
1 Bath
6 Guests
1097.92 ft²
- Breakfast
- Parking
- View
- Air Conditioner
US $76/Night
7 Nights - US $532
Hotel
- Maryland
- ·
- Central Maryland
- 0.56 mi to center
9.0Exceptional
(934 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $201/Night
7 Nights - US $1,408
House
- College Park
- ·
- Hillandale
- 0.54 mi to center
8.0Excellent
(1 Review)
1 Bedroom
3 Baths
6 Guests
1292 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $212/Night
7 Nights - US $1,486
Apartment
- College Park
- ·
- Langley Park
- 0.26 mi to center
8.2Excellent
(21 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $107/Night
7 Nights - US $749
House
- College Park
- ·
- White Oak
- 0.27 mi to center
1 Bedroom
4 Baths
15 Guests
1615 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $467/Night
7 Nights - US $3,272
House
- College Park
- ·
- Hillandale
- 0.54 mi to center
1 Bedroom
3 Baths
6 Guests
1615 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $341/Night
7 Nights - US $2,387
House
- College Park
- ·
- Calverton
- 0.56 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $186/Night
7 Nights - US $1,300
House
- College Park
- ·
- Silver Spring
- 1.79 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $179/Night
7 Nights - US $1,250
Large Private Villas in Hillandale
Over 23+ Large Villas in or Near Hillandale for Groups and Families
House
- College Park
- ·
- Fairland
- 1.95 mi to center
10.0Exceptional
(7 Reviews)
6 Bedrooms
3 Baths
10 Guests
3700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $360/Night
7 Nights - US $2,522
House
- College Park
- ·
- Fairland
- 1.93 mi to center
9.2Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
3401.4 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $429/Night
7 Nights - US $3,002
House
- College Park
- ·
- Calverton
- 0.38 mi to center
5 Bedrooms
3 Baths
16 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $418/Night
7 Nights - US $2,927
Villa
- Maryland
- ·
- College Park
- 1.66 mi to center
6.8Good
(18 Reviews)
3 Bedrooms
2 Baths
7 Guests
2002.09 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $360/Night
7 Nights - US $2,521
House
- College Park
- ·
- Silver Spring
- 2.99 mi to center
1 Bedroom
4 Baths
16 Guests
2153 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $820/Night
7 Nights - US $5,739
House
- College Park
- ·
- White Oak
- 1.55 mi to center
10.0Exceptional
(191 Reviews)
5 Bedrooms
3 Baths
12 Guests
3250 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $393/Night
7 Nights - US $2,753
Bed & Breakfast
- Maryland
- ·
- College Park
- 2.48 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
12 Guests
2000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $259/Night
7 Nights - US $1,811
House
- College Park
- ·
- Hillandale
- 0.59 mi to center
8.8Fabulous
(34 Reviews)
6 Bedrooms
1 Bath
10 Guests
1250 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $433/Night
7 Nights - US $3,028
House
- College Park
- ·
- White Oak
- 0.77 mi to center
8.0Excellent
(5 Reviews)
7 Bedrooms
3 Baths
16 Guests
3500 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $237/Night
7 Nights - US $1,659
Wheelchair Accessible Holiday Homes in Hillandale
Over 24+ Wheelchair Accessible Villas and Holiday Homes in or Near Hillandale
House
- College Park
- ·
- Calverton
- 0.19 mi to center
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
1 Guest
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $85/Night
7 Nights - US $593
Hotel
- Maryland
- ·
- Central Maryland
- 0.62 mi to center
9.1Exceptional
(162 Reviews)
5 Baths
293.32 ft²
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $209/Night
7 Nights - US $1,461
Hotel
- College Park
- ·
- Berwyn
- 0.32 mi to center
9.4Exceptional
(1006 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $159/Night
7 Nights - US $1,113
Condo
- College Park
- ·
- Adelphi
- 0.39 mi to center
1 Bedroom
1 Bath
3 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $64/Night
7 Nights - US $445
Hotel
- College Park
- ·
- Berwyn
- 0.33 mi to center
9.0Exceptional
(511 Reviews)
6 Baths
383.91 ft²
- EV Charge Station
- Parking
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,088
Hotel
- College Park
- ·
- Hillandale
- 0.59 mi to center
9.0Exceptional
(756 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $147/Night
7 Nights - US $1,031
House
- Maryland
- ·
- College Park
- 1.79 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $268/Night
7 Nights - US $1,878
Hotel
- College Park
- ·
- Berwyn
- 0.28 mi to center
8.5Fabulous
(261 Reviews)
1 Bath
367.77 ft²
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $161/Night
7 Nights - US $1,125
Hotel
- College Park
- ·
- Calverton
- 0.68 mi to center
8.3Excellent
(206 Reviews)
14 Baths
335.22 ft²
- EV Charge Station
- Parking
- Balcony/Terrace
- Air Conditioner
US $161/Night
7 Nights - US $1,127
Hillandale Villas, Airbnb and Holiday Homes Under $200
Over 77+ Hillandale Private Villas, Airbnb and Holiday Homes Under $200
Apartment
- College Park
- ·
- Berwyn
- 0.07 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Pet Friendly
US $169/Night
7 Nights - US $1,185
Apartment
- College Park
- ·
- Silver Spring
- 0.85 mi to center
8.9Fabulous
(51 Reviews)
1 Bedroom
1 Bath
3 Guests
936.46 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $119/Night
7 Nights - US $833
Hotel
- College Park
- ·
- Calverton
- 0.69 mi to center
8.8Fabulous
(1004 Reviews)
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $134/Night
7 Nights - US $935
Apartment
- College Park
- ·
- Takoma Park
- 0.54 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $168/Night
7 Nights - US $1,175
Apartment
- College Park
- ·
- Takoma Park
- 0.77 mi to center
8.8Fabulous
(16 Reviews)
1 Bedroom
1 Bath
3 Guests
7373.28 ft²
- Parking
- Air Conditioner
- Internet
Security/Safety
US $114/Night
7 Nights - US $797
New
Apartment
- College Park
- ·
- Silver Spring
- 2.44 mi to center
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $160/Night
7 Nights - US $1,123
New
Apartment
- College Park
- ·
- Silver Spring
- 1.98 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $101/Night
7 Nights - US $707
House
- College Park
- ·
- Calverton
- 0.15 mi to center
4 Bedrooms
3 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
Bedding/Linens
US $193/Night
7 Nights - US $1,353
House
- College Park
- ·
- Fairland
- 1.68 mi to center
3 Bedrooms
2 Baths
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $151/Night
7 Nights - US $1,059
Instantly Bookable Villa Rentals in Hillandale
Over 64+ Instantly Bookable Private Villas in or Near Hillandale
House
- College Park
- ·
- Silver Spring
- 1.41 mi to center
9.4Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $257/Night
7 Nights - US $1,796
Apartment
- College Park
- ·
- Takoma Park
- 0.75 mi to center
9.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $272/Night
7 Nights - US $1,902
House
- College Park
- ·
- Silver Spring
- 1.84 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $549/Night
7 Nights - US $3,844
House
- College Park
- ·
- Silver Spring
- 2.22 mi to center
8.0Excellent
(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $542/Night
7 Nights - US $3,797
House
- College Park
- ·
- Fairland
- 1.82 mi to center
3 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $516/Night
7 Nights - US $3,615
House
- College Park
- ·
- Hillandale
- 0.52 mi to center
3 Bedrooms
2 Baths
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Bedding/Linens
US $384/Night
7 Nights - US $2,689
House
- College Park
- ·
- Langley Park
- 0.46 mi to center
3 Bedrooms
2 Baths
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $133/Night
7 Nights - US $929
House
- College Park
- ·
- Hillandale
- 0.18 mi to center
3 Bedrooms
2 Baths
5 Guests
1725 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $131/Night
7 Nights - US $920
New
Apartment
- College Park
- ·
- Silver Spring
- 3.02 mi to center
9.8Exceptional
(6 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $321/Night
7 Nights - US $2,250
Book a Last Minute Place to Stay in Hillandale
About Hillandale Vacation Rentals
Discover over 196 amazing vacation rental options in Hillandale with pickleball courts or nearby facilities. From resorts to hotels, villas to condos, PickleTrip connects you with a vast selection of pickleball-ready amenities at great prices, providing you with the perfect spot to base your next pickleball vacation. Stay and Play pickleball When You Travel and uncover great stays in Hillandale.
Find exclusive last-minute deals on vacation rentals, resorts, and hotels with private courts and nearby facilities with PickleTrip™, whether you're traveling solo or with a group. Our platform offers a variety of stay options, from vacation rentals to Airbnb-style properties, all with private pickleball courts or nearby facilities. Compare options from multiple suppliers with a single click to find the perfect stay that fits your budget and style. Places to stay near pickleball courts are an average of 634.92 ft², with prices averaging US $269 per night.
With PickleTrip™, you can easily search for and book your next pickleball vacation rental with courts or nearby facilities. Our platform connects you with the ideal holiday rental to create a lifetime of travel memories. Prices listed are often discounted versus rack rates, so you can secure your perfect place to stay today and get ready to play pickleball in Hillandale.
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Top Pickleball-Ready Accommodation Types in Hillandale
| Type | Count |
|---|---|
| Vacation Homes | 109 |
| Holiday Apartments | 46 |
| Cottages | 2 |
| Villas | 2 |
Use these Quick Filters to Find a Vacation Rental in Hillandale
★ Pro Tip: PickleTrip™ is a travel platform, connecting avid pickleball players and enthusiasts with a variety of vacation rentals, resorts, and hotels featuring private pickleball courts or nearby facilities. We curate a vast selection of properties from trusted sources, providing you with unbeatable options and pricing to find the perfect pickleball getaway. Experience unforgettable pickleball matches in Hillandale with PickleTrip™.
Weather in Hillandale, MD
View the weather forecast for Hillandale before booking your Hillandale Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Hillandale, MD
PickleTrip offers a large selection of top attractions around Hillandale . Research things to do on your vacation before you visit Hillandale.
Frequently Asked Questions About Hillandale?
What are the top vacation rentals, resorts, and hotels in Hillandale with Courts?
Experience the ultimate pickleball vacation with PickleTrip™. We offer a variety of premium rental properties, resorts, and hotels with private pickleball courts or nearby facilities in Hillandale. Whether you're a beginner or a seasoned player, we have the perfect destination for you to stay and play. Book now and discover the best pickleball vacation spots in Hillandale!
- One bedroom w Private Entrance close to DC
- Cherry Hill Park
- Unique Tiny House Studio [With Chickens] Near I-95, FDA, DC, VA
- Spacious and Family Friendly 6-bedrooms house in delightful Silver Spring.
- Modern 1-BR Apartment
- Luxury Private Pass Time Space
- Single home, 4 beds, 2 baths
- Cozy Studio Walk to Shops, Quick Drive to DC
- Group Getaway! Modern Silver Spring Home w/Yard
- Spacious 4-bedroom townhome with game room in Greenbelt MD
Which vacation rentals, resorts, or hotels in Hillandale is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Hillandale? With PickleTrip™, you'll have access to a wide selection of top-rated properties that offer private pickleball courts or nearby facilities. Make the most of you getaway and ace your A-game while you travel.
- Charming 3-bedroom house in lovely Silver Spring with AC
- Cozy 3BR Suite w Private Entry Mins to DC UMD
- Best Western Plus College Park Hotel
How many PickleTrip vacation rentals or resorts are available in Hillandale?
PickleTrip™ offers a diverse selection of properties with private pickleball courts or nearby facilities to enhance your pickleball experience on your next trip. With a combination of established great stays and new options in top locations, PickleTrip™ has over 196 properties listed in Hillandale in 2026, and the number only continues to grow. By consolidating listings from various providers, PickleTrip™ brings you the best luxury stays for a sporty, professional, and fun travel experience.
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