Country Club Estates Vacations from $444
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Country Club Estates Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Milwaukee-West Medical Center by IHG
Wauwatosa
Price was $605, price is now $444 per person
$444
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
7.8/10 Good! (1,014 reviews)
Room was fine, clean. Area is sketchy AF
Reviewed on Oct 19, 2025
Saint Kate - The Arts Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $1,152, price is now $735 per person
$735
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Spacious room, comfortable bed. Love that when you check in they give you a glass of wine. The bar downstairs is a vibe and stays busy but did not disturb the quietness when I was in my room. Loved the art area in the hotel, I got to meet a local artist. This hotel is located near a lot of restaurants and stores within walkable distance. I parked the rental car and basically walked everywhere.
Reviewed on Oct 24, 2025
Kinn Guesthouse Bay View
Bay View
Save 100% on your flight
Price was $807, price is now $534 per person
$534
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (418 reviews)
Great location. Easy check in and clean room.
Reviewed on Oct 26, 2025
The Brewhouse Inn & Suites
Westown
Price was $826, price is now $618 per person
$618
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.4/10 Exceptional! (1,013 reviews)
The property and rooms are beautiful, especially if you are a beer enthusiast as the building is the former Pabst historic brewhouse. The surrounding area takes advantage of this theme, including breweries within a stone’s throw of the hotel.
Reviewed on Oct 19, 2025
Country Club Estates Hotel Deals
Harbor Shores on Lake Geneva
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $157 total per night from Oct 30 to Oct 31
$157 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (1,300 reviews)
I would love to revisit the property
Reviewed on Oct 26, 2025
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
$193 nightly
The price is $215 total per night from Nov 4 to Nov 5
$215 total
Nov 4 - Nov 5
Total with taxes and fees
8.6/10 Excellent! (3,017 reviews)
Our room was really clean for the most part and the people were very friendly, but the window screens in our room had holes in them, so there were bugs in our windows and a couple of flies in our room that we could not get rid of that were annoying. It didn’t seem that crowded, but there were no ...
Reviewed on Oct 25, 2025
Abbey Resort and Avani Spa
269 Fontana Boulevard, Fontana, WI
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $157 total per night from Oct 30 to Oct 31
$157 total
Oct 30 - Oct 31
Total with taxes and fees
8.4/10 Very Good! (1,611 reviews)
Room was clean and nice. The entire campus very nice. Great place to stay. Convenient to the Sailing Club. May want to replace mattresses. A little lumpy and worn but certainly clean and acceptable.
Reviewed on Oct 21, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.