Pigeon Bay Cottages - Vacation Rentals in Uptown
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Luxury Places to Stay in Uptown
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Top-Rated Vacation Rentals with a Pool in Uptown
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Pet-Friendly Vacation Rentals in Uptown
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Large Vacation Homes & Villas in Uptown
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Wheelchair Accessible Vacation Homes in Uptown
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Uptown Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Uptown
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About Uptown Vacation Rentals
With more than 92 Uptown vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Pigeonbaycottages 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 Uptown.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Pigeonbaycottages Uptown, 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 Uptown. Places to stay near Uptown are 886.39 ft² on average, with prices averaging US $303 a night.
Pigeonbaycottages makes it easy and safe to find and compare vacation rentals in Uptown 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 Uptown
| Type | Count |
|---|---|
| Holiday Apartments | 68 |
| Vacation Homes | 11 |
| Hotels | 1 |
Use these Quick Filters to Find a Vacation Rental in Uptown
★ Pro Tip: Pigeonbaycottages makes it easy to compare the best listings on Pigeonbaycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Pigeonbaycottages 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 Uptown.
Weather in Uptown
View the weather forecast for Uptown before booking your Uptown Vacation Rentals to confirm your best time to go.
Other Places to Stay Near Uptown, IL
Uptown Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Uptown?
There are a lot of options in Uptown. If you plan on staying in the Uptown area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Uptown:
- W3 - Spacious 2BR Apt + Free On-site Parking
- W2 - ❤️ New and Clean! Big Apartment with Parking
- Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
- Uptown Gem
- -Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Music-Inspired 2BR Garden Flat in Historic Uptown Near Legendary Music Venues
- Ultra-modern 4BR/2.5BA Uptown/Edgewater duplex, featuring a rooftop deck with fire pit and easy access to the lake, dining, shopping, and Chicago’s cultural highlights.
- Chic Vintage Stay w/Private Balcony – Walk to Argyle Redline, Lake, Dining
- Steps to the Lakefront! This Uptown Beauty is Everything You Need for a Perfect Chicago Getaway condo
Which vacation homes in Uptown are best for families?
If you are looking for a family-friendly vacation home in Uptown, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Uptown:
How many vacation rentals are available in Uptown?
Currently, the total number of properties listed in 2026 is over 92 in the Uptown area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Uptown.
