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Cloudland Vacation Packages

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Cloudland Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Chattanooga/Hamilton Place

Days Inn by Wyndham Chattanooga/Hamilton Place

2 out of 5
Price was $524, price is now $467 per person
$467
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Book a stay at this business-friendly motel in Chattanooga. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Place Mall and Regal Hamilton Place are located nearby.

Hotel Indigo Chattanooga - Downtown by IHG

Hotel Indigo Chattanooga - Downtown by IHG

3.5 out of 5
Price was $748, price is now $622 per person
$622
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Book a stay at this business-friendly hotel in Chattanooga. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ruby Falls and Tennessee Aquarium are located nearby.

The Hotel Chalet at The Choo Choo

The Hotel Chalet at The Choo Choo

4 out of 5
Price was $890, price is now $753 per person
$753
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Stay at this hotel in Chattanooga. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ruby Falls and Chattanooga Choo Choo Historic District are located nearby.
Great experience. I felt like I had stepped back in time but with all the modern amenities! We stayed in a railcar and it was very clean.

Reviewed on Sep 25, 2026

Lookout Mountain Riverview Inn

Lookout Mountain Riverview Inn

2 out of 5
Price was $832, price is now $712 per person
$712
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Stay at this guesthouse in Chattanooga. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ruby Falls and Lookout Mountain Incline Railway are located nearby.
Was Leary of a phone check in vs someone on site, but it was fine. Very communicative via cell. We were suppose to get a free bottle of wine, but it wasn’t in the room so there’s that…… it was a good deal for the money, would stay again

Reviewed on Sep 26, 2026

Hotel Clemons

Hotel Clemons

3 out of 5
Price was $731, price is now $634 per person
$634
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Stay at this hotel in Chattanooga. Enjoy a business center, concierge services, and a pool table. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ruby Falls and Tennessee Aquarium are located nearby.

Holiday Inn Express & Suites Chattanooga (East Ridge) by IHG

Holiday Inn Express & Suites Chattanooga (East Ridge) by IHG

2.5 out of 5
Price was $626, price is now $547 per person
$547
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Book a stay at this business-friendly hotel in Chattanooga. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hamilton Place Mall and Topgolf Chattanooga are located nearby.

Country Aire Bed & Breakfast

Country Aire Bed & Breakfast

3 out of 5
Price was $745, price is now $673 per person
$673
per person
Oct 31 - Nov 5
found 24 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chattanooga (CHA)
Stay at this B&B in Rock Spring. Enjoy free WiFi, free parking, and a picnic area. Popular attractions Helicopter Park and Walker County Regional Heritage Museum are located nearby.
Four of us stayed for one night. Beds were comfortable, property was quiet and the kids enjoyed the chickens, goats and horses. The property was close enough to Rock City for us. The only thing I would have to add it is not a Bed and Breakfast. They have stopped serving breakfast there according to a sign on the refrigerator and it wasn’t until we arrived that we found out.

Reviewed on Sep 20, 2026

Woodwose Cabin - Adventures Now

Woodwose Cabin - Adventures Now

3 out of 5
Price was $702, price is now $634 per person
$634
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chattanooga (CHA)
Stay at this cabin in Benton. Enjoy free WiFi and free parking. Popular attractions Sunburst Adventures and Outdoor Adventure Rafting are located nearby.
Quiet, spacious, many commodities, comfortable, AC and heating in good working condition, well equipped.

Reviewed on Oct 24, 2025

Cloudland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Indigo Chattanooga - Downtown by IHG

Hotel Indigo Chattanooga - Downtown by IHG

3.5 out of 5
Downtown Chattanooga
Price was $748, price is now $622 per person
$622
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
The Hotel Chalet at The Choo Choo

The Hotel Chalet at The Choo Choo

4 out of 5
Downtown Chattanooga
Price was $890, price is now $753 per person
$753
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Lookout Mountain Riverview Inn

Lookout Mountain Riverview Inn

2 out of 5
Price was $832, price is now $712 per person
$712
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)
Hotel Clemons

Hotel Clemons

3 out of 5
Downtown Chattanooga
Price was $731, price is now $634 per person
$634
per person
Nov 19 - Nov 23
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Chattanooga (CHA)

Cloudland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Chattanooga-Hamilton Place

La Quinta Inn & Suites by Wyndham Chattanooga-Hamilton Place

3 out of 5
Hamilton Place
Price was $633, price is now $557 per person
$557
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chattanooga (CHA)
Hotel Clemons

Hotel Clemons

3 out of 5
Downtown Chattanooga
Price was $803, price is now $655 per person
$655
per person
Oct 31 - Nov 5
found 17 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chattanooga (CHA)
Country Aire Bed & Breakfast

Country Aire Bed & Breakfast

3 out of 5
Price was $745, price is now $673 per person
$673
per person
Oct 31 - Nov 5
found 24 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Chattanooga (CHA)
The Hotel Chalet at The Choo Choo

The Hotel Chalet at The Choo Choo

4 out of 5
Downtown Chattanooga
Price was $2,307, price is now $2,029 per person
$2,029
per person
Nov 6 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chattanooga (CHA)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

American Airlines
Tue, Oct 13 - Sat, Oct 17
ORD
O'Hare Intl.
HSV
Huntsville Intl.
$271 Roundtrip, found 12 hours ago
$271
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 13 from O'Hare Intl. to Huntsville Intl., returning Sat, Oct 17, priced at $271 found 12 hours ago
Bargain Flight
Wed, Oct 21 - Wed, Nov 4
DFW
Dallas-Fort Worth Intl.
HSV
Huntsville Intl.
$281 Roundtrip, found 16 hours ago
$281
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Wed, Oct 21 from Dallas-Fort Worth Intl. to Huntsville Intl., returning Wed, Nov 4, priced at $281 found 16 hours ago
United
Sat, Oct 24 - Tue, Nov 10
ORD
O'Hare Intl.
CHA
Chattanooga Metropolitan
$299 Roundtrip, found 22 hours ago
$299
Roundtrip
found 22 hours ago
Select United flight, departing Sat, Oct 24 from O'Hare Intl. to Chattanooga Metropolitan, returning Tue, Nov 10, priced at $299 found 22 hours ago
Bargain Flight
Wed, Nov 11 - Tue, Dec 15
LAX
Los Angeles Intl.
HSV
Huntsville Intl.
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Select Bargain Flight flight, departing Wed, Nov 11 from Los Angeles Intl. to Huntsville Intl., returning Tue, Dec 15, priced at $309 found 2 days ago