Windsor
2 guests

Adults:

2

Children:

0

Child’s age:

Windsor

Oct 27 - Oct 28 ·
2 guests

Holiday Cottages in Windsor

Windsor
2 guests

Adults:

2

Children:

0

Child’s age:

Over 10 stays assessed to highlight the standout picks

Navigation

1. Troutbeck

2. Berkshire Fall Chalet Sauna, Lake & Firepit

3. Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong

4. Lakefront Retreat Home- Swimming-Fishing-Boating

Cottage near Windsor

  • Guest favorite
Troutbeck Troutbeck

Troutbeck

515 Leedsville Road
72.0 km (44.8 mi) from Windsor
  • In-room breakfast
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Sauna
  • Outdoor swimming pool

Offering a sauna for a relaxing experience, Troutbeck Guest House Amenia villa is located a 25-minute walk from Harlem Valley Rail Trail. This country house features opportunities for lawn tennis, ping-pong, and billiard in the area, 3.8 km from Sharon Valley Historic District.

The villa with a heated pool will also provide you with a personal trainer and yoga instruction onsite. Treatment facilities feature facial treatments. For active guests, there are yoga, as well as a yoga room.

9.2
5 reviews
~ US$600 / night

Troutbeck

72.0 km (44.8 mi) from Windsor
  • In-room breakfast
  • Free parking
  • 24-hour reception
  • Air conditioning
  • Sauna
  • Outdoor swimming pool

Troutbeck

Offering a sauna for a relaxing experience, Troutbeck Guest House Amenia villa is located a 25-minute walk from Harlem Valley Rail Trail. This country house features opportunities for lawn tennis, ping-pong, and billiard in the area, 3.8 km from Sharon Valley Historic District.

The villa with a heated pool will also provide you with a personal trainer and yoga instruction onsite. Treatment facilities feature facial treatments. For active guests, there are yoga, as well as a yoga room.

9.2
5 reviews
From US$ 600 / night

Holiday Cottages in Windsor

  • Great deal
Berkshire Fall Chalet Sauna, Lake & Firepit Berkshire Fall Chalet Sauna, Lake & Firepit

Berkshire Fall Chalet Sauna, Lake & Firepit

1340 East Otis Road
49.8 km (30.9 mi) from Windsor
242
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Situated 25 minutes' walk from the 330-acre lake "Big Pond", Berkshire Fall Chalet Sauna, Lake & Firepit Otis entices guests to explore various tourist attractions in the area.

9.2
4 reviews

Berkshire Fall Chalet Sauna, Lake & Firepit

49.8 km (30.9 mi) from Windsor
242
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Berkshire Fall Chalet Sauna, Lake & Firepit

Situated 25 minutes' walk from the 330-acre lake "Big Pond", Berkshire Fall Chalet Sauna, Lake & Firepit Otis entices guests to explore various tourist attractions in the area.

9.2
4 reviews

Holiday Cottages in Windsor with Private Pool

  • Private beach
Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong

Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong

284 State Route 39
78.5 km (48.8 mi) from Windsor
11
  • BBQ facilities
  • Free parking
  • Security
  • Air conditioning
  • Billiard tables
  • Sun loungers

The beachfront Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong Villa New Fairfield is located 10 minutes' drive from Candlewood Lake and provides canyoning, ping-pong, and fisheries for active guests. Providing guests with Wi-Fi and a private parking lot, the 6-room chalet is 3.6 km from Squantz Pond State Park.

3.7
3 reviews

Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong

78.5 km (48.8 mi) from Windsor
11
  • BBQ facilities
  • Free parking
  • Security
  • Air conditioning
  • Billiard tables
  • Sun loungers

Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong

The beachfront Blue House, King Bed, Grill, Pool Table, Air Hockey, Ping Pong Villa New Fairfield is located 10 minutes' drive from Candlewood Lake and provides canyoning, ping-pong, and fisheries for active guests. Providing guests with Wi-Fi and a private parking lot, the 6-room chalet is 3.6 km from Squantz Pond State Park.

3.7
3 reviews

Luxury Holiday Cottages in Windsor

Lakefront Retreat Home- Swimming-Fishing-Boating Lakefront Retreat Home- Swimming-Fishing-Boating

Lakefront Retreat Home- Swimming-Fishing-Boating

8 West Shore Drive
51.9 km (32.2 mi) from Windsor
93
  • Cookware/ Kitchen utensils
  • Tea and coffee facilities
  • Heating
  • Garden area

Nestled a 10-minute drive from Buddha Ariyamett Aram Temple, Lakefront Retreat Home- Swimming-Fishing-Boating Bethlehem entices guests to explore various tourist destinations nearby.

Lakefront Retreat Home- Swimming-Fishing-Boating

51.9 km (32.2 mi) from Windsor
93
  • Cookware/ Kitchen utensils
  • Tea and coffee facilities
  • Heating
  • Garden area

Lakefront Retreat Home- Swimming-Fishing-Boating

Nestled a 10-minute drive from Buddha Ariyamett Aram Temple, Lakefront Retreat Home- Swimming-Fishing-Boating Bethlehem entices guests to explore various tourist destinations nearby.

Frequently Asked Questions

Which holiday cottages in Windsor are best for a family getaway?

The Lakefront Retreat Home and Blue House provide excellent options for families, offering spacious rooms and outdoor activities. You can enjoy swimming, fishing, and various games indoors.

Tip:

Book your stay during weekdays for lower rates and quieter surroundings.

What are the best holiday cottages in Windsor near historic attractions?

The Berkshire Fall Chalet and Troutbeck are both located near Windsor Castle, making it easy to explore this historic landmark. These cottages offer a unique balance of comfort and proximity to famous sites.

Tip:

Visit Windsor Castle on a weekday to avoid crowds and enjoy a more leisurely experience.

Which holiday cottages in Windsor are ideal for outdoor activities?

Lakefront Retreat Home boasts close access to water sports, while Berkshire Fall Chalet has great hiking trails nearby. Both cater to outdoor enthusiasts looking for adventure.

Tip:

Pack a picnic and head to nearby parks, like Home Park, to enjoy a full day outdoors.

Are there any holiday cottages in Windsor with private pools?

The Blue House features a pool table and outdoor space, allowing for fun family gatherings. While it does not have a pool, it offers significant recreational options for families.

Tip:

Plan a barbecue night at the Blue House for a memorable family experience in the outdoor area.

Which holiday cottages in Windsor are great for a romantic retreat?

Troutbeck and Berkshire Fall Chalet offer cozy settings perfect for couples. Their tranquil environments provide a perfect backdrop for a romantic getaway.

Tip:

Consider visiting in the fall when the foliage around Windsor adds romantic scenery.

Which budget-friendly holiday cottages are available in Windsor?

The Blue House offers affordable rates while providing spacious accommodations. The Lakefront Retreat Home also features competitive pricing for families looking to save.

Tip:

Book during off-peak seasons for the best deals, typically in late autumn and winter.

What are the top pet-friendly holiday cottages in Windsor?

The Blue House allows pets, making it a great choice for travelers with furry friends. Also, the Lakefront Retreat Home welcomes pets, enabling a fun experience for the entire family.

Tip:

Check specific pet policies ahead of time, especially if travelling with more than one dog or large breed.

What unique local experiences should I consider while staying in Windsor?

Explore the Windsor Great Park and enjoy a stroll among its stunning landscapes. Joining a guided tour of Windsor Castle offers insights into royal history and architecture.

Tip:

Arrive early for your castle tour to take advantage of fewer crowds and more available time.

How can I easily get around Windsor during my stay?

Windsor is compact, making walking or cycling ideal for getting to main attractions. There's also a local bus service that connects to nearby towns and areas.

Tip:

Rent a bike from local shops near the castle to enjoy a scenic ride along the River Thames.

What seasonal events should I not miss while in Windsor?

Visit during the annual Windsor Festival in September, which features music, arts, and cultural events. The Christmas lights switch-on in November is also a delightful event.

Tip:

Plan ahead for the Windsor Festival to secure tickets for popular performances and events.

Location