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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Middletown

The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
$197 nightly
The price is $219
Sep 3 - Sep 4
Total includes taxes and fees
The Captain Stannard
The Homestead
Relax in a spacious room with a large bed, seating area, and cozy fireplace.

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (82)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
The Homestead
Jay's Ranch
Relax by the pool in a tranquil oasis, where a warm welcome awaits.

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (44)
"This was an amazing stay. Renee is a great host. She is clean, personable, and professional. The home is very cozy, and while still a work in progress, the outdoor area is beautiful and teeming with potential. This is not a hotel or a motel, understanding this, do not expect the starchy atmosphere of those places, but instead appreciate the friendly, homely vibe. If you’re looking for somewhere reasonably priced, clean, and cozy, this is a great spot."
$109 nightly
The price is $125
Aug 5 - Aug 6
Total includes taxes and fees
Jay's Ranch
The Bevin House Bed & Breakfast
Relax in a serene poolside setting surrounded by lush greenery and shaded seating.

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (77)
"Welcoming, fun, and absolutely stunning! A cuddly turkey didn’t hurt either. "
$258 nightly
The price is $287
Aug 17 - Aug 18
Total includes taxes and fees
The Bevin House Bed & Breakfast
Westbrook Inn B&B
Relax in the serene outdoor patio area, surrounded by lush greenery and comfortable seating options.

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (155)
"My granddaughter and I had a lovely stay."
$206 nightly
The price is $228
Sep 2 - Sep 3
Total includes taxes and fees
Westbrook Inn B&B
James Pharmacy Bed & Breakfast
Relax in a classic room with a four-poster bed, flat-screen TV, and comfortable armchair.

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
James Pharmacy Bed & Breakfast
Higganum House B&B
Stroll through the serene grounds, surrounded by lush greenery and a well-manicured lawn.

Higganum House B&B

3.0 star property
Higganum House B&B
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Backyard with a gravel surface, wooden deck, and small shed, surrounded by a fence.

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

$856 nightly
The price is $969
Aug 5 - Aug 6
Total includes taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Thimble Islands Bed & Breakfast
Enjoy a romantic dinner for two on the balcony overlooking the water.

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"A beautiful, quiet home in a stunning setting run by two extremely gracious hosts. Breakfast on both days was excellent."
Thimble Islands Bed & Breakfast
The Connecticut River Valley Inn
Deluxe Room, 1 King Bed, Fireplace, Garden Area | Desk, blackout drapes, soundproofing, iron/ironing board

The Connecticut River Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (24)
"Charming Inn, "
The Connecticut River Valley Inn
Green Acres B&B
Relax by the clear pool surrounded by a deck with lounge chairs and umbrellas.

Green Acres B&B

3.0 star property
9.8 out of 10, Exceptional, (150)
"Gracious hosts, many amenities and the best breakfast!"
Green Acres 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 Middletown Hotel Reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

10/10 Excellent
"Nice hotel and great location."
Edward 1-night trip
Posted 11 hours ago
Omni New Haven Hotel at Yale

Frequently asked questions

What is the nightly rate for a B&B in Middletown?
Prices for B&Bs in Middletown often vary, but you can find a great deal from $125 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Middletown B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Middletown?
The best time to book a B&B in Middletown is during the vibrant summer months, particularly from June to August. This period is characterized by warm temperatures, typically ranging from the mid-70s to the low 90s Fahrenheit, making it ideal for those who enjoy outdoor activities and the lively atmosphere of summer festivals. Visitors can indulge in a variety of experiences, from exploring the scenic vineyards to enjoying local events that highlight the region's rich culture.

July stands out as the most popular month, drawing travelers eager to soak up the sun and participate in local celebrations. The atmosphere is electric, with a plethora of activities available, whether you're interested in hiking picturesque trails or savoring wine tastings at nearby wineries.

If you're looking for a more budget-friendly option, consider visiting in October. This month offers a unique charm with the fall foliage painting the landscape in beautiful hues, creating a picturesque backdrop for leisurely drives and peaceful hikes. The crowds are thinner, allowing for a more intimate experience with the local culture and scenery.
What is the difference between a Middletown B&B and a hotel?
Every Middletown B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Middletown B&Bs.