Holiday Benefits - Vacation Rentals in Windermere

Romantic Bush Setting, Private Studio Cottage, Amazing View From US $172
         

Huntlee Pool Luxe House From US $1,629
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Tuckers Lane Boutique Accommodation From US $280
         

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10.0 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Lindsay Hideaway - Serenity Now From US $341
         

10.0 (193 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Windermere

Over 148+ Luxury Places to Stay in or Near Windermere
Lovedale Harvest Views House From US $3,513
         

New
House
  • Air Conditioner
  • Balcony/Terrace
  • Child Friendly
Allawah Estate - Lovedale Hunter Valley From US $2,377
         

Grandview Estate - Stunning Views From US $1,612
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Paradise Manor on Serene Paradise Estate From US $1,566
         

New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Luxury Hunter Valley Estate From US $1,175
         

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9.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
The Nest | Games Barn | Cinema| Ponies From US $1,166
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Windermere

Over 39+ Top-Rated Vacation Rentals with a Pool in or Near Windermere
Englewood Ridge From US $458
         

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10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury homestead with pool and spa, Hunter Valley From US $529
         

Dalwood Country House - Has It All From US $853
         

9.8 (66 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Cedar Cottage - Amazing views, private jacuzzi From US $208
         

9.8 (48 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Dolina - Lovedale, Hunter Valley From US $1,094
         

9.8 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Bluegum Cottage - Private jacuzzi , very private bush views. From US $205
         

9.8 (27 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Windermere

Over 34+ Pet-Friendly Vacation Rentals in or Near Windermere
Cabins at LaPera Estate Lovedale Wedding Chapel From US $198
         

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9.5 (105 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Hunter Hideaway Cottages From US $173
         

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8.2 (71 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Koru Escapes Retreat From US $498
         

6.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Huntlee Heights Summa From US $607
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windermere

Over 44+ Large Vacation Homes & Villas in or Near Windermere
Lambs Valley Guesthouse From US $533
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Huntlee Haven Luxe From US $279
         

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9.9 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Wandin Valley Estate From US $129
         

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9.0 (41 Reviews)
Villa
  • Parking
  • Pool
  • TV
Nottage Cottage - Gateway to the vineyards From US $481
         

7.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Security/Safety

Wheelchair Accessible Vacation Homes in Windermere

Over 8+ Wheelchair Accessible Vacation Homes in or Near Windermere
The Boathouses at Leaves & Fishes From US $1,037
         

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9.2 (24 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Mercure Maitland Monte Pio From US $111
         

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New
Hotel
  • Air Conditioner
  • Parking
  • Pool
Burncroft Guesthouse From US $1,005
         

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8.6 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Old Maitland Inn - Rutherford From US $96
         

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8.3 (841 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hunter Gateway Motel From US $96
         

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8.0 (1259 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Maitland City Motel From US $84
         

7.5 (919 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Windermere Varoom and Airbnb Places to Stay Under $200

Over 33+ Windermere Varoom and Airbnb Places to Stay Under $200
The Blue Wren free wifi From US $58
         

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9.8 (5 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Security/Safety
The Table Guesthouse From US $127
         

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9.6 (184 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
POLEHOUSE COTTAGE - located at Hunter Valley From US $162
         

9.6 (176 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Maitland Getaway | Spa, EV Charger, Pet Friendly From US $175
         

7.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Holiday home From US $189
         

New
House
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Windermere

Over 46+ Instantly Bookable Vacation Homes in or Near Windermere
Escape to the Country From US $315
         

9.4 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hunter Valley Bercuti From US $711
         

About Windermere Vacation Rentals

With more than 157 Windermere vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidaybenefits and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windermere.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Holidaybenefits Windermere, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windermere. Places to stay near Windermere are 1203.18 ft² on average, with prices averaging $530 a night.

Holidaybenefits makes it easy and safe to find and compare vacation rentals in Windermere with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windermere

Type Count
Vacation Homes 88
B&B 19
Cottages 16
Hotels with Suites 13
Villas 10
Holiday Apartments 5
Cabin Rentals 3
Others 2
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windermere

Pro Tip: Holidaybenefits makes it easy to compare the best listings on Holidaybenefits homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidaybenefits homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windermere.

Weather in Windermere

View the weather forecast for Windermere before booking your Windermere Vacation Rentals to confirm your best time to go.

December - February
High 99°F       Low 68°F
March - May
High 98°F       Low 44°F
June - August
High 78°F       Low 36°F
September - November
High 93°F       Low 50°F