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Chester Vacation Packages

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Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Future Inns Halifax

Future Inns Halifax

3 out of 5
Price was $960, price is now $825 per person
$825
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this business-friendly hotel in Halifax. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.
Facility is older but clean. Our bathroom door stuck and there were a few times we didn't know if we'd be able to get the door open. Mentioned to staff but it wasn't addressed during our stay. Carpets need a good shampooing.

Reviewed on Oct 18, 2026

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

4.5 out of 5
Price was $3,056, price is now $2,405 per person
$2,405
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this luxury vacation home in Halifax. Enjoy free WiFi, free parking, and private pools. Popular attractions Halifax Waterfront Boardwalk and Scotiabank Centre are located nearby.
Everything was unique especially the automated system. Enjoyed the spa. We had some difficulty using the living room tv. Could not find local channels. Everything was LG channels. Otherwise the location, decor and amenities was extraordinary. We will tell our friends about this wonderful place.

Reviewed on Oct 5, 2026

Brewery Park Hotel

Brewery Park Hotel

3.5 out of 5
Price was $1,264, price is now $1,044 per person
$1,044
per person
Dec 28 - Jan 4
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Stay at this hotel in Halifax. Enjoy free WiFi, Netflix, and premium bedding. Popular attractions Halifax Waterfront Boardwalk and Casino Nova Scotia are located nearby.

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Price was $1,056, price is now $883 per person
$883
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this business-friendly hotel in Halifax. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Halifax Citadel are located nearby.

Red George Inn and Suites

Red George Inn and Suites

2 out of 5
Price was $1,168, price is now $977 per person
$977
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this family-friendly hotel in Halifax. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Halifax Waterfront Boardwalk and Scotiabank Centre are located nearby.
Great location and very responsive hosts. Historical rooms added a unique flair. Thanks for a great stay!

Reviewed on Oct 18, 2026

The Hollis Halifax a DoubleTree Suites by Hilton Hotel

The Hollis Halifax a DoubleTree Suites by Hilton Hotel

4 out of 5
Price was $1,240, price is now $1,045 per person
$1,045
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this business-friendly hotel in Halifax. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Halifax Waterfront Boardwalk and Scotiabank Centre are located nearby.

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was $1,095, price is now $929 per person
$929
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this business-friendly hotel in Dartmouth. Enjoy free WiFi, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Halifax Waterfront Boardwalk and Dartmouth Crossing are located nearby.
Loved the ‘vintage look’ - chandeliers, Victorian furniture throughout lobby & rooms. Enjoyed the complimentary coffee/ tea bar in lobby along with breakfast. Lovely, helpful female supervisor on when we were there. Great location. Thank you!

Reviewed on Oct 18, 2026

HFX Airport Hotel

HFX Airport Hotel

2.5 out of 5
Price was $1,040, price is now $888 per person
$888
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Book a stay at this family-friendly hotel in Goffs. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the restaurant in our reviews. Popular attractions Atlantic Canada Aviation Museum and Bennery Lake Nature Reserve are located nearby.
My daughter was traveling back to school after fall break by herself. They were very helpful. The shuttle to and from the airport was very helpful as well

Reviewed on Oct 18, 2026

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
HFX Airport Hotel

HFX Airport Hotel

2.5 out of 5
Price was $800, price is now $714 per person
$714
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

4.5 out of 5
Price was $1,446, price is now $1,182 per person
$1,182
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was $935, price is now $808 per person
$808
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
Price was $814, price is now $718 per person
$718
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)

Chester Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was $1,056, price is now $883 per person
$883
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

Seacliff- Best of Halifax -Luxury Waterfront Paradise -Pool, Hot Tub, Wharf & Boathouse

4.5 out of 5
Price was $3,056, price is now $2,405 per person
$2,405
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Brewery Park Hotel

Brewery Park Hotel

3.5 out of 5
North End
Price was $1,264, price is now $1,044 per person
$1,044
per person
Dec 28 - Jan 4
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
Red George Inn and Suites

Red George Inn and Suites

2 out of 5
Downtown Halifax
Price was $1,168, price is now $977 per person
$977
per person
Dec 28 - Jan 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)

Top Flight Deals

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

Flair Airlines
Mon, Feb 1 - Thu, Feb 18
YKF
Region of Waterloo Intl.
YHZ
Stanfield Intl.
$152 Roundtrip, found 1 hour ago
$152
Roundtrip
found 1 hour ago
Select Flair Airlines flight, departing Mon, Feb 1 from Region of Waterloo Intl. to Stanfield Intl., returning Thu, Feb 18, priced at $152 found 1 hour ago
Flair Airlines
Fri, Nov 20 - Mon, Nov 23
YYZ
Pearson Intl.
YHZ
Stanfield Intl.
$165 Roundtrip, just found
$165
Roundtrip
just found
Select Flair Airlines flight, departing Fri, Nov 20 from Pearson Intl. to Stanfield Intl., returning Mon, Nov 23, priced at $165 just found
Porter Airlines
Sun, Nov 8 - Tue, Dec 1
YYT
St. John's Intl.
YHZ
Stanfield Intl.
$378 Roundtrip, found 1 hour ago
$378
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Sun, Nov 8 from St. John's Intl. to Stanfield Intl., returning Tue, Dec 1, priced at $378 found 1 hour ago
Air Transat
Thu, Nov 26 - Thu, Nov 26
YOW
Macdonald-Cartier Intl.
YHZ
Stanfield Intl.
$420 Roundtrip, found 1 hour ago
$420
Roundtrip
found 1 hour ago
Select Air Transat flight, departing Thu, Nov 26 from Macdonald-Cartier Intl. to Stanfield Intl., returning Thu, Nov 26, priced at $420 found 1 hour ago