Main Street Historic District Vacation Packages for 2026

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Top Hotel Deals

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
30.88 km from Main Street Historic District
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
4.95 km from Main Street Historic District
Book a stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
5.61 km from Main Street Historic District
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff ...
The Watershed

The Watershed

3.5 out of 5
353 Main Ave Norwalk CT
28.44 km from Main Street Historic District
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
Hyatt House Shelton

Hyatt House Shelton

3 out of 5
830 Bridgeport Ave Shelton CT
30.43 km from Main Street Historic District
Book a stay at this business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
30.77 km from Main Street Historic District
Book a stay at this business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
21.81 km from Main Street Historic District
Book a stay at this spa hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
2.58 km from Main Street Historic District
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
27.69 km from Main Street Historic District
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Courtyard by Marriott Norwalk

Courtyard by Marriott Norwalk

3 out of 5
474 Main Ave Norwalk CT
27.24 km from Main Street Historic District
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff ...
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
26.77 km from Main Street Historic District
Book a stay at this business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hilton Garden Inn Norwalk

Hilton Garden Inn Norwalk

3 out of 5
560 Main Ave Norwalk CT
26.67 km from Main Street Historic District
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean rooms ...
Hampton Inn Danbury

Hampton Inn Danbury

2.5 out of 5
81 Newtown Rd Danbury CT
3.72 km from Main Street Historic District
Book a stay at this business-friendly hotel in Danbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hampton Inn by Hilton Shelton

Hampton Inn by Hilton Shelton

2.5 out of 5
695 Bridgeport Ave Shelton CT
30.51 km from Main Street Historic District
Book a stay at this business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Delamar Westport

Delamar Westport

4 out of 5
1595 Post Rd E Westport CT
30.86 km from Main Street Historic District
Stay at this hotel in Westport. Enjoy free breakfast, free valet parking, and free train station pick-up. Popular attractions Southport Beach and Burying Hill ...
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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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Avelo Airlines
Thu, Mar 19 - Mon, Mar 23
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 3 days ago
$118
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Thu, Mar 19 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Mon, Mar 23, priced at $118 found 3 days ago
Breeze Airways
Thu, May 7 - Mon, May 11
MCO
Orlando Intl.
HPN
Westchester County
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 7 from Orlando Intl. to Westchester County, returning Mon, May 11, priced at $127 found 4 days ago
JetBlue Airways
Thu, May 7 - Mon, May 11
MCO
Orlando Intl.
HPN
Westchester County
$156 Roundtrip, found 4 days ago
$156
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, May 7 from Orlando Intl. to Westchester County, returning Mon, May 11, priced at $156 found 4 days ago
American Airlines
Thu, May 7 - Mon, May 11
MCO
Orlando Intl.
HPN
Westchester County
$190 Roundtrip, found 4 days ago
$190
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, May 7 from Orlando Intl. to Westchester County, returning Mon, May 11, priced at $190 found 4 days ago
Delta
Wed, Apr 15 - Sat, Apr 18
TPA
Tampa Intl.
HPN
Westchester County
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 15 from Tampa Intl. to Westchester County, returning Sat, Apr 18, priced at $207 found 2 days ago