Find Romantic Hotels in Chester, CT from $112

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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, (2056)
"Great view from the room really enjoy the stay "
United States
Armagan
$185 nightly
The price is $209
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 $112
Dec 21 - Dec 22
Total with taxes and fees
Holiday Inn Norwich by IHG

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 15 - Dec 16
Total with taxes and fees
Inn at Harbor Hill Marina

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

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
$195 nightly
The price is $221
Dec 15 - Dec 16
Total with taxes and fees
Inn at Middletown

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (341)
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
$245 nightly
The price is $282
Jan 1 - Jan 2, 2026
Total with taxes and fees
Madison Beach Hotel

Baymont by Wyndham Branford/New Haven

Baymont by Wyndham Branford/New Haven
2.5 star property
Branford
6.6 out of 10, (1004)
"Good Breakfast, nice atmosphere "
United States
Jessie
$99 nightly
The price is $114
Dec 15 - Dec 16
Total with taxes and fees
Baymont by Wyndham Branford/New Haven

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

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1002)
"Wonderful stay in a beautiful setting."
United States
Deborah
$306 nightly
The price is $352
Dec 22 - Dec 23
Total with taxes and fees
Saybrook Point Resort & Marina

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.
$237 nightly
The price is $255
Dec 15 - Dec 16
Total with taxes and fees
PEACEFUL SPA ESCAPE MINUTES TO MOHEGAN SUN CASINO
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.

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