Windsor Pet Friendly Vacation Rentals
Cabin
- Kentucky
- ·
- Russell Springs
- 2.64 mi to center
10.0Exceptional
(22 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $254/Night
7 Nights - US $1,775
House
9.6Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
1280.91 ft²
- Fireplace/Heating
- Pet Friendly
Parking
Internet
US $94/Night
7 Nights - US $658
Cottage
1 Bedroom
1 Bath
Child Friendly
US $80/Night
7 Nights - US $560
Cabin
- Kentucky
- ·
- Russell Springs
- 3.21 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
1 Bath
6 Guests
Spa- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $244/Night
7 Nights - US $1,711
House
4 Bedrooms
2 Baths
8 Guests
1496.18 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Child Friendly
US $312/Night
7 Nights - US $2,182
Cabin
10.0Exceptional
(5 Reviews)
2 Bedrooms
1 Bath
8 Guests
1200 ft²
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $226/Night
7 Nights - US $1,582
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
495 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $204/Night
7 Nights - US $1,426
Cabin
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $192/Night
7 Nights - US $1,344
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
Air Conditioner- Internet
- Child Friendly
US $143/Night
7 Nights - US $1,002
Pet-Friendly Vacation Rentals in Windsor
Over 89+ Pet-Friendly Vacation Rentals in or Near Windsor
Cabin
9.4Exceptional
(39 Reviews)
1 Bedroom
1 Bath
4 Guests
364 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $187/Night
7 Nights - US $1,306
New
House
4 Bedrooms
2 Baths
22 Guests
2023.62 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $1,114/Night
7 Nights - US $7,798
Cabin
9.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $183/Night
7 Nights - US $1,280
New
House
4 Bedrooms
2 Baths
20 Guests
2023.62 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $969/Night
7 Nights - US $6,786
New
House
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $673/Night
7 Nights - US $4,708
New
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $438/Night
7 Nights - US $3,065
House
2 Bedrooms
1 Bath
10 Guests
1120 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $424/Night
7 Nights - US $2,970
New
House
- Kentucky
- ·
- Russell Springs
- 6.70 mi to center
1 Bedroom
4 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $420/Night
7 Nights - US $2,941
New
House
- Kentucky
- ·
- Russell Springs
- 4.54 mi to center
1 Bedroom
3 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $413/Night
7 Nights - US $2,888
Luxury Places to Stay in Windsor
Over 80+ Luxury Places to Stay in or Near Windsor
House
2 Bedrooms
1 Bath
10 Guests
1119.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $738/Night
7 Nights - US $5,164
New
House
2 Bedrooms
1 Bath
8 Guests
1119.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $705/Night
7 Nights - US $4,936
House
4 Bedrooms
2 Baths
20 Guests
2028 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $639/Night
7 Nights - US $4,473
House
4 Bedrooms
2 Baths
22 Guests
2028 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $634/Night
7 Nights - US $4,441
New
House
3 Bedrooms
1 Bath
10 Guests
1119.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $601/Night
7 Nights - US $4,205
House
8.0Excellent
(4 Reviews)
4 Bedrooms
4 Baths
20 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
US $598/Night
7 Nights - US $4,188
New
House
2 Bedrooms
1 Bath
8 Guests
1119.45 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $564/Night
7 Nights - US $3,948
House
5 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $489/Night
7 Nights - US $3,426
House
1 Bedroom
1 Bath
8 Guests
1119.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $441/Night
7 Nights - US $3,085
Top-Rated Vacation Rentals with a Pool in Windsor
Over 2+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
House
9.4Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
1800 ft²
Private Pool- Fireplace/Heating
Pool- Balcony/Terrace
US $335/Night
7 Nights - US $2,346
House
8.4Excellent
(8 Reviews)
5 Bedrooms
2 Baths
18 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $506/Night
7 Nights - US $3,542
Large Vacation Homes & Villas in Windsor
Over 31+ Large Vacation Homes & Villas in or Near Windsor
House
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $345/Night
7 Nights - US $2,416
House
1 Bedroom
1 Bath
10 Guests
1119.45 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $417/Night
7 Nights - US $2,921
House
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
12 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $299/Night
7 Nights - US $2,091
House
10.0Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $240/Night
7 Nights - US $1,683
House
10.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
10 Guests
1700 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $378/Night
7 Nights - US $2,647
Cabin
- Kentucky
- ·
- Russell Springs
- 6.65 mi to center
9.2Exceptional
(164 Reviews)
4 Bedrooms
3 Baths
12 Guests
2826 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $336/Night
7 Nights - US $2,354
Cabin
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $143/Night
7 Nights - US $999
House
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
12 Guests
1800 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $384/Night
7 Nights - US $2,686
Cabin
9.6Exceptional
(183 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $268/Night
7 Nights - US $1,875
Wheelchair Accessible Vacation Homes in Windsor
Over 1+ Wheelchair Accessible Vacation Homes in or Near Windsor
Hotel
- Kentucky
- ·
- Russell Springs
- 1.81 mi to center
5.8Average
(97 Reviews)
4 Baths
150.69 ft²
Breakfast- Pet Friendly
- Parking
- Internet
US $80/Night
7 Nights - US $560
Windsor Petfriendly and Airbnb Homes Under $200
Over 17+ Windsor Petfriendly and Airbnb Homes Under $200
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
768 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $171/Night
7 Nights - US $1,194
Cabin
9.6Exceptional
(10 Reviews)
3 Bedrooms
2 Baths
8 Guests
1280 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $140/Night
7 Nights - US $977
Cabin
10.0Exceptional
(53 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $150/Night
7 Nights - US $1,050
Cabin
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $121/Night
7 Nights - US $849
Cabin
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $121/Night
7 Nights - US $849
New
House
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $131/Night
7 Nights - US $918
New
House
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $126/Night
7 Nights - US $881
Cottage
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $179/Night
7 Nights - US $1,251
Cottage
9.6Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $120/Night
7 Nights - US $839
Instantly Bookable Vacation Homes in Windsor
Over 25+ Instantly Bookable Vacation Homes in or Near Windsor
New
House
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $413/Night
7 Nights - US $2,893
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $267/Night
7 Nights - US $1,871
Cabin
9.8Exceptional
(19 Reviews)
3 Bedrooms
2 Baths
8 Guests
2160 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $335/Night
7 Nights - US $2,342
House
10.0Exceptional
(8 Reviews)
3 Bedrooms
1 Bath
6 Guests
770 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $243/Night
7 Nights - US $1,698
House
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1200 ft²
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $333/Night
7 Nights - US $2,328
Ski Chalet
9.8Exceptional
(47 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $202/Night
7 Nights - US $1,416
House
4 Bedrooms
1 Bath
10 Guests
1100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $205/Night
7 Nights - US $1,436
House
2 Bedrooms
1 Bath
8 Guests
1120 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $400/Night
7 Nights - US $2,802
New
House
- Kentucky
- ·
- Russell Springs
- 3.65 mi to center
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $260/Night
7 Nights - US $1,819
Book a Last Minute Place to Stay in Windsor
About Windsor Vacation Rentals
There are more than 243 places to stay in Windsor and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Windsor.
Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Windsor, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Windsor. Places to stay near Windsor are 947.13 ft² on average, with prices averaging US $373 a night.
PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Windsor with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.
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Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Windsor
| Type | Count |
|---|---|
| Vacation Homes | 160 |
| Cottages | 9 |
| Holiday Apartments | 2 |
| Villas | 1 |
Use these Quick Filters to Find a Vacation Rental in Windsor
★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Windsor.
Weather in Windsor, KY
View the weather forecast for Windsor before booking your hotel or rental.
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
Frequently Asked Questions About Windsor?
What are the top vacation rentals in Windsor?
Find the best options in or near Windsor for pet-friendly travel. If you are planning a trip or vacation in Windsor, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Windsor:
- Nancy Kentucky 1800s log cabin
- Beautiful cabin nestled in the woods surrounded by water
- Sandy Acres Cabins (Big Cabin) - by Galilean Home
- Sandy Acres Hobbit - Near Galilean Home - Liberty
- Farmhouse in the Lake Cumberland area
- Lake Cumberland Cabin Getaway! Quick Local Lake Access!
- Beautiful Cubby Cabin On The Mountain
- The Haven on Lakeshore Drive
- Big Foot's Retreat- is in walking distance of Cumberland Point Recreation Area
- 3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland
Which vacation homes in Windsor are best for families?
Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Windsor? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Windsor:
How many PetFriendly vacation rentals are available in Windsor?
PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 243 in the Windsor area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Windsor.
People Also Ask
Finding the best prices in Windsor
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