Find Romantic Hotels in Chester, CT from $111

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Mohegan Sun

Mohegan Sun
4.5 star property
Montville
9.2 out of 10, Wonderful, (2055)
"Great view from the room really enjoy the stay "
United States
Armagan
$201 nightly
The price is $228
Jan 4 - Jan 5, 2026
Total with taxes and fees
Mohegan Sun

Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG
3.0 star property
Westside Norwich
7.6 out of 10, Good, (1000)
"Great stay will definitely come back "
United States
Hilda V
$97 nightly
The price is $111
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Norwich by IHG

Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (540)
"Clean room, friendly staff. "
United States
Katharine
$161 nightly
The price is $182
Dec 28 - Dec 29
Total with taxes and fees
Inn at Middletown

Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
3.0 star property
Wallingford
8.8 out of 10, Excellent, (1002)
"Surprisingly beautiful hotel! "
United States
Lisa
$119 nightly
The price is $136
Dec 22 - Dec 23
Total with taxes and fees
Hilton Garden Inn Wallingford/Meriden

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (339)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
$244 nightly
The price is $281
Jan 1 - Jan 2, 2026
Total with taxes and fees
Madison Beach Hotel

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1000)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$159 nightly
The price is $183
Dec 14 - Dec 15
Total with taxes and fees
Inn at Harbor Hill Marina

Sheraton Hartford South Hotel

Sheraton Hartford South Hotel
3.5 star property
Rocky Hill
8.4 out of 10, Very Good, (1003)
"Very clean room, inviting lobby, and very nice employees at check in and checkout "
United States
Caroline
$105 nightly
The price is $121
Dec 21 - Dec 22
Total with taxes and fees
Sheraton Hartford South Hotel

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (47)
"Small but clean and cozy! Not impressed just another apartment. Spa and pool very nice. I would return. "
United States
Johnny B.
$236 nightly
The price is $254
Dec 16 - Dec 17
Total with taxes and fees
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO

All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
$271 nightly
The price is $288
Dec 13 - Dec 14
Total with taxes and fees
All New Private and Cozy in great location

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
$209 nightly
The price is $233
Dec 14 - Dec 15
Total with taxes and fees
Westbrook Inn B&B
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 out more about Chester

Chester attractions for couples

Chester, Connecticut, offers a charming blend of history and nature that will captivate adventurous travelers. Start your exploration at the Chester Historical Society, where you can dive into the region's rich past with engaging exhibits that highlight local heritage. For outdoor enthusiasts, the nearby Cockaponset State Forest provides a wealth of hiking trails that meander through picturesque landscapes, perfect for family outings. Don’t miss a visit to the Chester Gallery, an art space showcasing local and regional artists, where you can find unique pieces that embody the essence of the area. For a taste of Chester’s culinary scene, dine at The Spice Club, known for its creative fusion of global flavors and locally sourced ingredients, making every meal a delightful experience. As for accommodations, consider staying in the charming downtown area, where boutique hotels offer personalized service and a cozy atmosphere, ensuring you feel pampered after a day of adventure. With its welcoming vibe and attention to detail, Chester is a delightful place for travelers seeking quality and a unique experience.

Top Chester Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need a romantic vacation, we've got just the ticket. If you'd like to explore some of the area's notable sights, you might make a stop by Connecticut River, Norma Terris Theater, or Connecticut Valley Railroad State Park Trail. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Chester?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Chester is 54 inches.
What is there to do in Chester?
There's nothing better than seeing a new destination with your sweetheart, so consider checking out all that Chester has to offer. Connecticut River, Norma Terris Theater, and Connecticut Valley Railroad State Park Trail are worth a stop when you're out and about.
What's the best way to get to Chester and around town during my romantic getaway?
This information about transportation options in Chester might help your romantic trip get off to a smooth start: Make your way to Chester with a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is the closest major airport located 23.1 mi (37.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia