Bolton Vacations from $239

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Your Bolton Vacation

Say bye-bye to the hassle of planning and hello to a Bolton vacation package. With your travel details organized before you go, you can focus on discovering the best of this city, starting with Downtown Hartford, which is great for shopping, families and festivals. If your trip to Bolton includes some sightseeing, don't miss renowned attractions like Nathan Hale Homestead, Manchester Parkade and Tallwood Country Club. Expedia will help you escape the everyday. Tailor your vacation to Bolton to suit your travel style, whatever that may be.

The Latest Bolton vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Save 100% on your flight
Price was $344, price is now $239 per person
$239
per person
Dec 11 - Dec 14
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (1,164 reviews)
Noisy - mostly because of road but the facility itself was really nice and I loved the room itself

Reviewed on Oct 19, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $399, price is now $293 per person
$293
per person
Dec 11 - Dec 14
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
The bar downstairs is so fun, and their pizza night provided us with the best pizza in New Haven (better than the famous spots we all know). The bartenders made our trip, and showed us the warmth of the people of New Haven. Do not skip the bar! Even if you do not drink, the games are great and the food is even better.

Reviewed on Oct 17, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $564, price is now $418 per person
$418
per person
Dec 11 - Dec 14
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (21 reviews)
The apartment was very clean, well maintained and beautiful decor. The golf simulator was much enjoyed by my son. It's close to the train station, but more of a 20 minute walk to the center of Yale. If you are looking for space and comfort, this is a great place, but just not as close to Yale as other options (though close to Yale medical school).

Reviewed on Sep 16, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $435, price is now $340 per person
$340
per person
Dec 11 - Dec 14
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.4/10 Very Good! (1,016 reviews)
Everything was great!

Reviewed on Oct 18, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $708, price is now $563 per person
$563
per person
Dec 24 - Dec 29
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Access to airport and service for my early Lyft was great

Reviewed on Oct 17, 2025

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Bolton Hotel Deals

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd, Hartford, CT
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (1,025 reviews)
"Our room was great & the breakfast was delicious!"

Reviewed on Oct 19, 2025

Best Western Hartford Hotel & Suites
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Oct 26 to Oct 27
$118 total
Oct 26 - Oct 27
Total with taxes and fees
7.4/10 Good! (1,042 reviews)
"Perfect for our stay convenient location"

Reviewed on Oct 18, 2025

The Capitol Hotel
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
185 Ella Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $74 total per night from Nov 5 to Nov 6
$74 total
Nov 5 - Nov 6
Total with taxes and fees
6.6/10 (1,608 reviews)
"Great Front desk staff, customer services oriented."

Reviewed on Oct 14, 2025

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
See all 511 properties in Bolton
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.

Find the Best Bolton Vacation Packages

Bolton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Xfinity Theatre, Connecticut Science Center and Crystal Lake Sandy Beach

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Frequently asked questions

How much does a Bolton vacation package cost?
You can snap up a vacation package to this top destination from $239 on Expedia. However, how much your vacation to Bolton costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Bolton?
December, January and February are the best times to search for cheap Bolton vacation packages. Choosing to travel in quieter months means you can usually find better prices on accommodations and flights.
How many days is enough for Bolton?
Generally, a handful of days is enough to see the main attractions during your Bolton vacation. But if you want to have more time to unwind or take day trips, think about extending your itinerary.
How to find the best Bolton package deals?
Use Expedia's filter tool to find some terrific Bolton package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Bolton package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Bolton vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a personalized Bolton vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Bolton?
If you're planning a spur-of-the-moment Bolton trip, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Bolton vacation packages?
If you're anything like us, you love going away but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Bolton trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.