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Guilford Vacation Packages

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Guilford Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $599, price is now $490 per person
$490
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $859, price is now $632 per person
$632
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
my fav. vacation place!!!

Reviewed on Aug 27, 2026

Inn at Middletown

Inn at Middletown

3.5 out of 5
Price was $1,033, price is now $785 per person
$785
per person
Oct 11 - Oct 16
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Book a stay at this business-friendly hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions General Mansfield House and Harbor Park are located nearby.

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,531, price is now $1,945 per person
$1,945
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer.

Reviewed on Aug 27, 2026

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,479, price is now $1,182 per person
$1,182
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Book a stay at this spa hotel in West Hartford. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions PeoplesBank Arena and The Meadows Music Theatre are located nearby.

Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $829, price is now $667 per person
$667
per person
Oct 29 - Nov 2
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Book a stay at this family-friendly apartment in Vernon. Enjoy free parking, a fitness center, and a fireplace in the lobby. Popular attractions Arts Center East and Shoppes at Buckland Hills are located nearby.
Our stay was very good. Way better than staying at a hotel. Would definitely do it again.

Reviewed on Aug 9, 2026

Solano Inn

Solano Inn

2.5 out of 5
Price was $878, price is now $715 per person
$715
per person
Oct 11 - Oct 16
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Stay at this hotel in Portland. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Arrigoni Winery and Harbor Park are located nearby.
Tucked away in a quiet, but gorgeous, area. Nice restaurants nearby. Great spot - will definitely be back.

Reviewed on Aug 27, 2026

Belden House & Mews

Belden House & Mews

5 out of 5
Save 100% on your flight
Price was $1,892, price is now $1,542 per person
$1,542
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Book a stay at this luxury hotel in Litchfield. Enjoy free WiFi, free valet parking, and an outdoor pool. Popular attractions Litchfield Town Green and Big Cathedral Trail are located nearby.

Guilford Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $859, price is now $632 per person
$632
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
Delamar West Hartford

Delamar West Hartford

4 out of 5
Save 100% on your flight
Price was $1,052, price is now $768 per person
$768
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $829, price is now $667 per person
$667
per person
Oct 29 - Nov 2
found 21 hours ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $842, price is now $682 per person
$682
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)

Guilford Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Inn at Middletown

Inn at Middletown

3.5 out of 5
Washington Street Historic District
Price was $1,033, price is now $785 per person
$785
per person
Oct 11 - Oct 16
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,531, price is now $1,945 per person
$1,945
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
Landing Apartments Vernon

Landing Apartments Vernon

3.5 out of 5
Price was $1,189, price is now $940 per person
$940
per person
Oct 6 - Oct 12
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
Landing in Downtown Hartford Near Dunkin' Park

Landing in Downtown Hartford Near Dunkin' Park

3.5 out of 5
Downtown Hartford
Price was $1,078, price is now $865 per person
$865
per person
Oct 6 - Oct 12
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)

Top Flight Deals

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

Breeze Airways
Fri, Oct 9 - Mon, Oct 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$147 Roundtrip, just found
$147
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Oct 9 from Orlando Intl. to Bradley Intl., returning Mon, Oct 12, priced at $147 just found
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$182 Roundtrip, just found
$182
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $182 just found
Frontier Airlines
Wed, Sep 23 - Mon, Oct 12
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$192 Roundtrip, just found
$192
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 23 from Luis Munoz Marin Intl. to Bradley Intl., returning Mon, Oct 12, priced at $192 just found
Bargain Flight
Wed, Oct 28 - Sun, Nov 1
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$231 Roundtrip, found 4 days ago
$231
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Wed, Oct 28 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sun, Nov 1, priced at $231 found 4 days ago