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Book Middletown Bed & Breakfast

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Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Compare 11 B&B in Middletown with updated reviews, rates, and availability.

The Captain Stannard
LED TV

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (227)
"Very nice place and the owners are super people and treat their customers very well! I loved it here and would definitely stay here again!"
$252 nightly
The price is $280
Jun 22 - Jun 23
Total includes taxes and fees
The Captain Stannard
Jay's Ranch
Exterior

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (41)
"Quiet and safe "
$109 nightly
The price is $125
Jun 24 - Jun 25
Total includes taxes and fees
Jay's Ranch
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7) | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (80)
"Beautiful and comfortable b+b. Well thought out amenities such as comfortable bed, fluffy towels, great breakfast options and snacks. The innkeepers friendly and made sure we were well taken care of during our stay "
The Homestead
The Bevin House Bed & Breakfast
Seasonal outdoor pool, pool umbrellas, sun loungers

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (74)
"Welcoming, fun, and absolutely stunning! A cuddly turkey didn’t hurt either. "
$260 nightly
The price is $289
Jun 19 - Jun 20
Total includes taxes and fees
The Bevin House Bed & Breakfast
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (150)
"Beautiful bed and breakfast with plush robes and slippers, super clean, would stay again!"
$286 nightly
The price is $318
Jun 22 - Jun 23
Total includes taxes and fees
Westbrook Inn B&B
James Pharmacy Bed & Breakfast
Miss Anna James Room | 1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
$532 nightly
The price is $578
Jun 19 - Jun 20
Total includes taxes and fees
James Pharmacy Bed & Breakfast
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Property grounds

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

$863 nightly
The price is $976
Jun 19 - Jun 20
Total includes taxes and fees
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Higganum House B&B
Exterior

Higganum House B&B

3.0 star property
Higganum House B&B
Thimble Islands Bed & Breakfast
Porch

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
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
Seasonal outdoor pool

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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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.