Bolton Vacations from $452

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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.
Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
Save 100% on your flight
Price was $582, price is now $452 per person
$452
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,002 reviews)
The location was right off the highway ....easy to find

Reviewed on Sep 3, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,414, price is now $1,485 per person
$1,485
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
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 $1,405, price is now $1,035 per person
$1,035
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 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 $1,149, price is now $852 per person
$852
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.2/10 Wonderful! (865 reviews)
Really close to Yale. No on site parking so we had to search for parking and walk back to the hotel late at night after we arrived…and there were some iffy characters around the area. More iffy characters greeted us near our parked car at 8:30am the next morning. The best part was Kristina at the front desk! She was really friendly and helpful.

Reviewed on Aug 31, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Save 100% on your flight
Price was $644, price is now $498 per person
$498
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (869 reviews)
No issues! Clean, convenient & friendly staff. 15-20 walk to bars and restaurants

Reviewed on Sep 1, 2025

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Bolton Hotel Deals

The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $106 total per night from Sep 18 to Sep 19
$106 total
Sep 18 - Sep 19
Total with taxes and fees
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
$67 nightly
The price is $77 total per night from Sep 7 to Sep 8
$77 total
Sep 7 - Sep 8
Total with taxes and fees
Days Inn by Wyndham Windsor Locks / Bradley Intl Airport
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
351 Pitkin Steet, East Hartford, CT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $140 total per night from Sep 21 to Sep 22
$140 total
Sep 21 - Sep 22
Total with taxes and fees
Hampton Inn & Suites Hartford/East Hartford
See all 486 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.

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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 $452 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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