Douglas pickleball Stays, Resort Rentals, & Homes
House
- Massachusetts
- ·
- Webster
- 1.92 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
1 Bath
13 Guests
Parking
Ocean View
Balcony/Terrace
View
US $592/Night
7 Nights - US $4,144
House
- Massachusetts
- ·
- Northbridge
- 2.68 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
6 Guests
699.65 ft²
- Parking
Air Conditioner
Internet
Security/Safety
US $159/Night
7 Nights - US $1,113
Bed & Breakfast
- Connecticut
- ·
- Thompson
- 1.41 mi to center
10.0Exceptional
(40 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Kitchen- Air Conditioner
US $221/Night
7 Nights - US $1,548
House
- Providence
- ·
- Burrillville
- 1.91 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1411 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $511/Night
7 Nights - US $3,579
House
- Providence
- ·
- Burrillville
- 1.91 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1410.07 ft²
- Hot Tub
- Parking
- Air Conditioner
- Internet
US $439/Night
7 Nights - US $3,073
Apartment
- Providence
- ·
- Bridgeton
- 0.42 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
Laundry
Bedding/Linens
US $155/Night
7 Nights - US $1,083
House
- Providence
- ·
- Pascoag
- 0.22 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Balcony/Terrace
- Air Conditioner
- Internet
- Laundry
US $403/Night
7 Nights - US $2,823
House
- Connecticut
- ·
- Rogers
- 8.77 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $189/Night
7 Nights - US $1,322
House
- Connecticut
- ·
- Thompson
- 3.20 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
4 Guests
825 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $578/Night
7 Nights - US $4,043
Luxury Places to Stay in Douglas
Over 107+ Luxury Places to Stay in or Near Douglas
Cottage
- Connecticut
- ·
- Putnam
- 2.18 mi to center
1 Bedroom
1 Bath
- Parking
- Ocean View
- Balcony/Terrace
- View
US $904/Night
7 Nights - US $6,329
New
House
- Massachusetts
- ·
- Worcester
- 2.31 mi to center
4 Bedrooms
2 Baths
10 Guests
2500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $829/Night
7 Nights - US $5,800
House
- Massachusetts
- ·
- Milford
- 1.61 mi to center
4 Bedrooms
1 Bath
16 Guests
2300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $743/Night
7 Nights - US $5,200
House
- Connecticut
- ·
- Putnam
- 2.04 mi to center
10.0Exceptional
(8 Reviews)
5 Bedrooms
2 Baths
10 Guests
2363 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $677/Night
7 Nights - US $4,740
Apartment
- Massachusetts
- ·
- Worcester
- 2.06 mi to center
3 Bedrooms
2 Baths
6 Guests
398.26 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $664/Night
7 Nights - US $4,648
House
- Massachusetts
- ·
- Webster
- 0.78 mi to center
9.8Exceptional
(20 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $608/Night
7 Nights - US $4,253
Apartment
- Massachusetts
- ·
- Webster
- 1.05 mi to center
9.8Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $550/Night
7 Nights - US $3,851
House
- Massachusetts
- ·
- Northbridge
- 2.94 mi to center
9.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1919 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $540/Night
7 Nights - US $3,781
House
- Massachusetts
- ·
- Oxford
- 1.30 mi to center
6.3Good
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
2604.87 ft²
- Parking
Pool- Internet
Child Friendly
US $491/Night
7 Nights - US $3,437
Top-Rated Villas with a Pool in Douglas
Over 10+ Top-Rated Private Villas with a Pool in or Near Douglas
Apartment
- Connecticut
- ·
- Rogers
- 9.92 mi to center
9.8Exceptional
(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $275/Night
7 Nights - US $1,923
House
- Massachusetts
- ·
- Oxford
- 1.06 mi to center
9.6Exceptional
(9 Reviews)
3 Bedrooms
2 Baths
6 Guests
2600 ft²
Private Pool- Parking
- Pool
- Kitchen
US $258/Night
7 Nights - US $1,808
Apartment
8.8Fabulous
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
800 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $163/Night
7 Nights - US $1,141
Hotel
8.6Fabulous
(1001 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Kitchen
US $118/Night
7 Nights - US $827
House
- Massachusetts
- ·
- Worcester
- 2.94 mi to center
3 Bedrooms
1 Bath
5 Guests
2002.09 ft²
- Parking
- Pool
- Internet
- Child Friendly
US $402/Night
7 Nights - US $2,814
House
- Massachusetts
- ·
- Webster
- 1.45 mi to center
10.0Exceptional
(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
1800 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $620/Night
7 Nights - US $4,340
Hotel
- Connecticut
- ·
- Thompson
- 1.60 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $425/Night
7 Nights - US $2,978
House
- Massachusetts
- ·
- Uxbridge
- 2.03 mi to center
4.5Average
(7 Reviews)
4 Bedrooms
3 Baths
6 Guests
- Pool
- View
- Kitchen
- Air Conditioner
US $200/Night
7 Nights - US $1,400
House
- Massachusetts
- ·
- Worcester
- 2.94 mi to center
3 Bedrooms
1 Bath
5 Guests
2000 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $397/Night
7 Nights - US $2,781
Pet-Friendly Villas in Douglas
Over 25+ Pet-Friendly Private Villas in or Near Douglas
New
House
- Connecticut
- ·
- Thompson
- 3.24 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $247/Night
7 Nights - US $1,731
House
- Connecticut
- ·
- Thompson
- 3.24 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
753.47 ft²
- Parking
Pet Friendly- Child Friendly
Sports/Activities
US $175/Night
7 Nights - US $1,224
House
- Massachusetts
- ·
- Webster
- 1.67 mi to center
9.6Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
8 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $378/Night
7 Nights - US $2,643
Bed & Breakfast
- Connecticut
- ·
- Thompson
- 1.42 mi to center
9.8Exceptional
(67 Reviews)
6 Bedrooms
5 Baths
13 Guests
301.39 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $316/Night
7 Nights - US $2,215
House
2 Bedrooms
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $231/Night
7 Nights - US $1,617
New
House
- Massachusetts
- ·
- Worcester
- 2.68 mi to center
2 Bedrooms
1 Bath
4 Guests
1553 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $268/Night
7 Nights - US $1,877
Apartment
- Providence
- ·
- Woonsocket
- 1.72 mi to center
2 Bedrooms
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $38/Night
7 Nights - US $267
Apartment
- Providence
- ·
- Woonsocket
- 0.91 mi to center
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $222/Night
7 Nights - US $1,556
Apartment
- Providence
- ·
- Woonsocket
- 1.38 mi to center
2 Bedrooms
1 Bath
4 Guests
750 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $131/Night
7 Nights - US $918
Large Private Villas in Douglas
Over 10+ Large Villas in or Near Douglas for Groups and Families
Apartment
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
11 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $422/Night
7 Nights - US $2,952
Villa
- Massachusetts
- ·
- Worcester
- 2.55 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
5 Guests
1797.57 ft²
- Parking
- View
- Air Conditioner
- Internet
US $227/Night
7 Nights - US $1,587
Villa
- Connecticut
- ·
- Thompson
- 1.67 mi to center
5 Bedrooms
5 Baths
12 Guests
- Balcony/Terrace
- Internet
- Child Friendly
TV
US $1,725/Night
7 Nights - US $12,075
House
- Connecticut
- ·
- Putnam
- 2.04 mi to center
5 Bedrooms
2 Baths
10 Guests
2368.06 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $333/Night
7 Nights - US $2,329
House
- Sturbridge
- ·
- Dudley
- 1.81 mi to center
10.0Exceptional
(17 Reviews)
4 Bedrooms
3 Baths
10 Guests
1800 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $464/Night
7 Nights - US $3,245
House
- Massachusetts
- ·
- Worcester
- 2.86 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $952/Night
7 Nights - US $6,661
Villa
- Massachusetts
- ·
- Charlton
- 2.38 mi to center
8.8Fabulous
(26 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $299/Night
7 Nights - US $2,096
House
5 Bedrooms
3 Baths
10 Guests
- Child Friendly
- Security/Safety
US $1,061/Night
7 Nights - US $7,428
House
- Massachusetts
- ·
- Worcester
- 2.99 mi to center
5 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $996/Night
7 Nights - US $6,970
Wheelchair Accessible Holiday Homes in Douglas
Over 9+ Wheelchair Accessible Villas and Holiday Homes in or Near Douglas
House
- Connecticut
- ·
- Thompson
- 1.41 mi to center
6 Bedrooms
6 Baths
14 Guests
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $499/Night
7 Nights - US $3,493
House
- Massachusetts
- ·
- Northbridge
- 2.82 mi to center
9.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
20655.94 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $252/Night
7 Nights - US $1,764
Hotel
8.6Fabulous
(732 Reviews)
1 Bath
- Breakfast
- Parking
- Kitchen
- Air Conditioner
US $111/Night
7 Nights - US $774
Hotel
8.4Excellent
(234 Reviews)
7 Baths
301.39 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $160/Night
7 Nights - US $1,118
Hotel
8.2Excellent
(421 Reviews)
6 Baths
263.71 ft²
- Breakfast
EV Charge Station- Parking
- Air Conditioner
US $172/Night
7 Nights - US $1,201
Hotel
8.0Excellent
(261 Reviews)
2 Baths
200.93 ft²
- Parking
- Air Conditioner
- Internet
Wheelchair Accessible
US $194/Night
7 Nights - US $1,361
Hotel
7.4Very Good
(591 Reviews)
3 Baths
301.39 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $164/Night
7 Nights - US $1,149
Hotel
7.1Very Good
(34 Reviews)
1 Bath
3229.17 ft²
- Breakfast
- Parking
- Air Conditioner
- Internet
US $107/Night
7 Nights - US $749
Hotel
6.4Good
(125 Reviews)
14 Baths
279.86 ft²
- EV Charge Station
- Parking
- Kitchen
- Air Conditioner
US $140/Night
7 Nights - US $980
Douglas Villas, Airbnb and Holiday Homes Under $200
Over 34+ Douglas Private Villas, Airbnb and Holiday Homes Under $200
House
- Connecticut
- ·
- Rogers
- 8.75 mi to center
9.6Exceptional
(24 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $188/Night
7 Nights - US $1,315
Apartment
- Massachusetts
- ·
- Northbridge
- 2.68 mi to center
8.5Fabulous
(8 Reviews)
3 Bedrooms
1 Bath
5 Guests
645.83 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $152/Night
7 Nights - US $1,065
Hotel
- Providence
- ·
- Woonsocket
- 0.41 mi to center
6.8Good
(258 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $95/Night
7 Nights - US $664
House
- Connecticut
- ·
- Thompson
- 1.89 mi to center
9.4Exceptional
(39 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,356
House
3 Bedrooms
2 Baths
5 Guests
1797.57 ft²
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $159/Night
7 Nights - US $1,113
Apartment
- Massachusetts
- ·
- Northbridge
- 2.68 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
5 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $177/Night
7 Nights - US $1,236
Apartment
- Massachusetts
- ·
- Northbridge
- 2.53 mi to center
7.4Very Good
(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $168/Night
7 Nights - US $1,177
Apartment
- Massachusetts
- ·
- Worcester
- 1.96 mi to center
2 Bedrooms
1 Bath
4 Guests
950 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $180/Night
7 Nights - US $1,258
Apartment
- Massachusetts
- ·
- Milford
- 1.47 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $133/Night
7 Nights - US $934
Instantly Bookable Villa Rentals in Douglas
Over 24+ Instantly Bookable Private Villas in or Near Douglas
Apartment
- Massachusetts
- ·
- Uxbridge
- 2.41 mi to center
10.0Exceptional
(15 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $256/Night
7 Nights - US $1,794
US $329/Night
7 Nights - US $2,303
Apartment
9.8Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $477/Night
7 Nights - US $3,336
Apartment
1 Bedroom
1 Bath
1 Guest
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $128/Night
7 Nights - US $894
House
- Sturbridge
- ·
- Dudley
- 2.77 mi to center
9.4Exceptional
(13 Reviews)
3 Bedrooms
2 Baths
5 Guests
1200 ft²
Oceanfront- Parking
- Ocean View
- Balcony/Terrace
US $238/Night
7 Nights - US $1,667
House
- Massachusetts
- ·
- Worcester
- 2.71 mi to center
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $395/Night
7 Nights - US $2,764
House
- Massachusetts
- ·
- Webster
- 2.07 mi to center
10.0Exceptional
(12 Reviews)
3 Bedrooms
2 Baths
8 Guests
1200 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $394/Night
7 Nights - US $2,760
New
Apartment
- Providence
- ·
- Bridgeton
- 0.34 mi to center
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $123/Night
7 Nights - US $858
Cottage
- Connecticut
- ·
- Putnam
- 3.38 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $168/Night
7 Nights - US $1,179
Book a Last Minute Place to Stay in Douglas
About Douglas Vacation Rentals
Discover over 116 amazing vacation rental options in Douglas 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 Douglas.
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 820.66 ft², with prices averaging US $315 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 Douglas.
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Top Pickleball-Ready Accommodation Types in Douglas
| Type | Count |
|---|---|
| Vacation Homes | 52 |
| Holiday Apartments | 35 |
| Cottages | 7 |
| Villas | 3 |
Use these Quick Filters to Find a Vacation Rental in Douglas
★ 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 Douglas with PickleTrip™.
Weather in Douglas, MA
View the weather forecast for Douglas before booking your Douglas Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 30°F
March - May
High 77°F Low 36°F
June - August
High 88°F Low 60°F
September - November
High 80°F Low 36°F
Top Attractions Around Douglas, MA
PickleTrip offers a large selection of top attractions around Douglas . Research things to do on your vacation before you visit Douglas.
Other Places to Stay in Douglas, MA
Frequently Asked Questions About Douglas?
What are the top vacation rentals, resorts, and hotels in Douglas 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 Douglas. 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 Douglas!
- Family-friendly 5-Bedroom Webster Home w/Cozy Balcony - Perfect for Families!
- The Watson Boutique Bed & Breakfast
- Rustic Log Cabin on the Lake
- SteamPunk Bunk House and Intergalactic Way Station
- Zen Inspired Retreat with Private Forest Trails
- 3-bedroom house on Webster Lake with amazing views, beach and boat launch access
- Lakefront Getaway-Hot Tub + Kayaks + Paddleboards
- Quintessential New England Home w/Patio & Grill!
- Direct Lakefront Retreat | Indian Ranch | Casinos
- Fully Renovated all season lakefront Home with beautiful views all year round!
Which vacation rentals, resorts, or hotels in Douglas is best for families looking for a pickleball-getaway?
Looking for a fun and active getaway with pickleball courts in Douglas? 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.
How many PickleTrip vacation rentals or resorts are available in Douglas?
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 116 properties listed in Douglas 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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