Cottage Romance - Vacation Rentals in Windermere

Cabins at LaPera Estate Lovedale Wedding Chapel From US $198
         

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9.5 (101 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Tuckers Lane Boutique Accommodation From US $320
         

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10.0 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
t“Romantic Countryside Escape – Cozy Hot Tub & Scenic Views” From US $269
         

Cedar Cottage - Amazing views, private jacuzzi From US $223
         

9.8 (49 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Windermere

Over 155+ 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
         

Luxury Hunter Valley Estate From US $1,785
         

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9.8 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Grandview Estate - Stunning Views From US $1,735
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Huntlee Pool Luxe House From US $1,629
         

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8.0 (1 Review)
House
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Paradise Manor on Serene Paradise Estate From US $1,566
         

New
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Windermere

Over 43+ Top-Rated Vacation Rentals with a Pool in or Near Windermere
Lindsay Hideaway - Serenity Now From US $376
         

10.0 (199 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury homestead with pool and spa, Hunter Valley From US $505
         

Englewood Ridge From US $458
         

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10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Nest | Games Barn | Cinema| Ponies From US $1,166
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Dolina - Lovedale, Hunter Valley From US $1,178
         

9.8 (31 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windermere

Over 36+ Pet-Friendly Vacation Rentals in or Near Windermere
Hunter Valley Modern 4-Bedroom House From US $373
         

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10.0 (3 Reviews)
House
  • 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
Hearth Haven Retreat on Triton From US $458
         

Cosy Villa With Mountain Views From US $329
         

New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Maitland Getaway | Spa, EV Charger, Pet Friendly From US $204
         

7.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windermere

Over 48+ Large Vacation Homes & Villas in or Near Windermere
Tuckers Lane Boutique Accommodation From US $843
         

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9.6 (136 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Wandin Valley Estate From US $132
         

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9.2 (47 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 $122
         

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7.8 (283 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Burncroft Guesthouse From US $1,005
         

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8.6 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hunter Gateway Motel From US $94
         

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8.2 (1320 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Maitland Inn - Rutherford From US $96
         

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8.2 (811 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Maitland City Motel From US $90
         

7.4 (985 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Windermere Vacation Rentals and Airbnb Places to Stay Under $200

Over 35+ Windermere Vacation Rentals and Airbnb Places to Stay Under $200
Leconfield House, luxury in the Hunter, Pokolbin, 150yrs in 2022 From US $199
         

10.0 (6 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Leconfield House From US $197
         

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9.9 (31 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
The Table Guesthouse From US $136
         

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9.6 (184 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
POLEHOUSE COTTAGE - located at Hunter Valley From US $178
         

9.6 (178 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Holiday Home From US $200
         

4.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Leconfield House, luxury and heritage hotels in Pokolbin Hunter Valley From US $179
         

10.0 (5 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Heritage country luxury hotels close to wineries, concerts & restaurants From US $179
         

10.0 (1 Review)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Instantly Bookable Vacation Homes in Windermere

Over 51+ Instantly Bookable Vacation Homes in or Near Windermere
Leconfield House, heritage, Pokolbin Hunter Valley, built in 1872,150yrs in 2022 From US $331
         

10.0 (8 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Leconfield House, Pokolbin, Hunter Valley luxury, built in 1872, 150yrs in 2022 From US $331
         

10.0 (6 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Plumstead Guesthouse – entire house in Lovedale wine country From US $200
         

9.8 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Escape to the Country From US $340
         

9.2 (12 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pool
Hunter Valley Bercuti From US $591
         

About Windermere Vacation Rentals

With more than 34 Windermere vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Cottageromance 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 Cottageromance 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 751.48 ft² on average, with prices averaging US $409 a night.

Cottageromance 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
Cottages 16
Villas 10
Cabin Rentals 4
Vacation Homes 3
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windermere

Pro Tip: Cottageromance makes it easy to compare the best listings on Cottageromance homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cottageromance 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

Windermere Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Windermere?
How many vacation rentals are available in Windermere?

Currently, the total number of properties listed in 2026 is over 34 in the Windermere area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windermere.