Cottage Romance - Vacation Rentals in Windermere

Bluegum Cottage - Private jacuzzi , very private bush views. From US $236
         

9.8 (29 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Cabins at LaPera Estate Lovedale Wedding Chapel From US $198
         

|
9.4 (106 Reviews)
Ski Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly
Tuckers Lane Boutique Accommodation From US $320
         

|
10.0 (6 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
POLEHOUSE COTTAGE - located at Hunter Valley From US $200
         

9.6 (182 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
Lochinvar Hunter Valley Cottage From US $246
         

10.0 (94 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Windermere

Over 147+ Luxury Places to Stay in or Near Windermere
Luxury Hunter Valley Estate From US $1,785
         

|
10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Noble Willow Estate From US $1,591
         

|
5.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
The Boathouses at Leaves & Fishes From US $1,037
         

|
9.1 (27 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Burncroft Guesthouse From US $1,005
         

|
6.8 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Noble Willow Homestead From US $903
         

|
9.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Hearth Haven Retreat on Triton From US $709
         

Huntlee Heights From US $662
         

New
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
Tranquil Vale Vineyard From US $152
         

|
9.5 (88 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Lamp Estate From US $610
         

9.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Englewood Ridge From US $540
         

|
8.9 (28 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Wandin Valley Estate From US $127
         

|
8.8 (132 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lochinvar House From US $240
         

8.7 (55 Reviews)
Bed & Breakfast
  • Parking
  • Pool
  • TV
Hunter Gateway Motel From US $94
         

|
8.2 (1313 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Old Maitland Inn - Rutherford From US $96
         

|
8.2 (804 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Windermere

Over 35+ Pet-Friendly Vacation Rentals in or Near Windermere
Lindsay Hideaway - Serenity Now From US $362
         

10.0 (202 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Hunter Valley Modern 4-Bedroom House From US $373
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Englewood Ridge From US $458
         

|
10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Greta Getaway From US $180
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cedar Cottage - Amazing views, private jacuzzi From US $223
         

9.8 (50 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Pet Friendly
Winders Estate | Relax, Retreat, Reconnect From US $612
         

9.8 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windermere

Over 42+ Large Vacation Homes & Villas in or Near Windermere
Wandin Valley Estate From US $128
         

|
9.2 (49 Reviews)
Villa
  • Parking
  • Pool
  • TV
Lambs Valley Guesthouse From US $344
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Leconfield House, heritage accommodation, Pokolbin Hunter Valley, 150yrs in 2022 From US $1,116
         

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

Wheelchair Accessible Vacation Homes in Windermere

Over 3+ Wheelchair Accessible Vacation Homes in or Near Windermere
Maitland City Motel From US $90
         

7.4 (983 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Mercure Maitland Monte Pio From US $123
         

|
7.8 (283 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Windermere Vacation Rentals and Airbnb Places to Stay Under $200

Over 28+ Windermere Vacation Rentals and Airbnb Places to Stay Under $200
Lovedale farm Stay From US $166
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
The Table Guesthouse From US $136
         

|
9.6 (185 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Plumstead Guesthouse – entire house in Lovedale wine country From US $197
         

9.8 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Peaceful Farm Stay Close to Vineyards From US $121
         

9.0 (2 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Self contained country cottage set on 40 acres From US $155
         

4.9 (7 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Self contained country cottage set on 40 acres From US $155
         

4.6 (7 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Self contained country cottages set on 40 acres From US $159
         

4.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Rosebrook Eco Tiny Home From US $184
         

5.0 (2 Reviews)
House
  • Air Conditioner
  • Bedding/Linens
  • Kitchen

Instantly Bookable Vacation Homes in Windermere

Over 53+ Instantly Bookable Vacation Homes in or Near Windermere
Leconfield House, heritage, Pokolbin Hunter Valley, built in 1872,150yrs in 2022 From US $328
         

10.0 (8 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Leconfield House, luxury in the Hunter, Pokolbin, 150yrs in 2022 From US $212
         

10.0 (7 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Leconfield House, Pokolbin, Hunter Valley luxury, built in 1872, 150yrs in 2022 From US $284
         

10.0 (6 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Hunter Valley Bercuti From US $427
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • TV
Unique Rockhouse, private jacuzzi, bush views From US $220
         

9.8 (24 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pool

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 $410 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.