Search Romantic Hotels in Chester

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Check availability on Chester Romantic Hotels

Tonight
21 Dec - 22 Dec
Tomorrow
22 Dec - 23 Dec
Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan

Our top choices for Chester romantic hotels

Casino
Mohegan Sun

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
The price is 4.372.764 ₫
5.685.356 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Mohegan Sun
Terrace/patio
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG
3.0 star property
Westside Norwich
7.6 out of 10, Good, (1003)
"Great stay will definitely come back "
United States
Hilda V
The price is 2.657.815 ₫
3.056.487 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Holiday Inn Norwich by IHG
Exterior
Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden

Hilton Garden Inn Wallingford/Meriden
3.0 star property
Wallingford
8.8 out of 10, Excellent, (1001)
"Clean room and staff wonderful "
United States
Liliana
The price is 3.019.120 ₫
3.471.988 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Hilton Garden Inn Wallingford/Meriden
Front of property – evening/night
Inn at Middletown

Inn at Middletown

Inn at Middletown
3.5 star property
Washington Street Historic District
9.0 out of 10, Wonderful, (543)
"The Inn was very nice!"
United States
Traci
The price is 4.298.818 ₫
5.469.836 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Inn at Middletown
Property grounds
Inn at Harbor Hill Marina

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
The price is 4.184.085 ₫
4.811.698 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Inn at Harbor Hill Marina
Exterior
Madison Beach Hotel

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
The price is 6.453.491 ₫
7.421.515 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Madison Beach Hotel
Courtyard
Sheraton Hartford South Hotel

Sheraton Hartford South Hotel

Sheraton Hartford South Hotel
3.5 star property
Rocky Hill
8.4 out of 10, Very good, (1001)
"Very clean room, inviting lobby, and very nice employees at check in and checkout "
United States
Caroline
The price is 2.763.075 ₫
3.177.536 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Sheraton Hartford South Hotel
Property grounds
The Spa at Norwich Inn

The Spa at Norwich Inn

The Spa at Norwich Inn
3.5 star property
Norwich
8.8 out of 10, Excellent, (1001)
"Great place!"
United States
Jill
The Spa at Norwich Inn
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (176)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is 5.840.614 ₫
6.483.081 ₫ total
includes taxes & fees
22 Dec - 23 Dec
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.
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Top Chester Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need some romantic time away, we've got just the thing. 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're interested in staying close to a certain attraction, you can sort properties by neighbourhood and proximity 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, take a look at these details about year-round temperatures in Chester: The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 2°C. Average annual precipitation for Chester is 1382 mm.
What is there to do in Chester?
There's nothing better than wandering around 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 centre. If you'd like to venture out around the area, you may want a rental car for your journey.