Middletown Vacation Rentals

Name: Family Stays: Middletown, CT
Price range: $230 total

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Vacation Rentals in Middletown

Large Charming Historic House close to Beaches

Clinton CT

With a stay at this vacation home in Clinton, you'll be near the beach, just a 4-minute walk from Adam Stanton House and General Store Museum and 12 minutes by foot from Clinton Town Beach.

Kitchen

Washer

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

New Britain CT

$218 nightly

$246 total

Dec 7 - Dec 8

Total with taxes and fees

Located in New Britain, this vacation home is within a 5-minute drive of Lincoln Technical Institute and New Britain Stadium.

Kitchen

Washer

Gorgeous 4BR Beach House with Private Beach Access.

Branford CT

With a stay at this vacation home, you'll be centrally located in Branford, within a 15-minute drive of Yale University and Foote Memorial Park Tennis Center.

Kitchen

Washer

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Guilford CT

A stay at this vacation home places you in the heart of Guilford, within a 5-minute drive of Guilford Town Green and Hyland House Museum.

Pool

Kitchen

Private Apartment in Berlin

Berlin CT

$279 nightly

$316 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home in Berlin, you'll be within a 5-minute drive of Webster Square Shopping Center and New Britain Stadium.

Kitchen

Washer

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford CT

With a stay at this vacation home in Branford (Branford Center), you'll be within a 15-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

Waterfront Beach House

Clinton CT

Located in Clinton, this vacation home is by the ocean, within a 5-minute drive of Clinton Plaza Shopping Center and Adam Stanton House and General Store Museum.

Kitchen

Washer

Modern Family Retreat | Near Downtown Hartford | Sleeps 10

Bloomfield CT

$607 nightly

$688 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home in Bloomfield, you'll be within a 5-minute drive of Bloomfield Crossing and Gillette Ridge Golf Course.

Kitchen

Washer

Capt Nathaniel Clarke Historic Homestead,Reunions, Magnificent Yard

Old Saybrook CT

$550 nightly

$623 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

A stay at this vacation home places you in the heart of Old Saybrook, within a 5-minute drive of Saybrook Country Barn and General William Hart House.

Kitchen

Washer

Cozy Lakefront Bungalow w firepit/dock/kayaks

Plymouth CT

Located in Plymouth, this vacation home is on the waterfront, within a 15-minute drive of Black Rock State Park and Rockwell Park.

Hot Tub

Kitchen

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

Windsor CT

With a stay at this vacation home in Windsor, you'll be within a 5-minute drive of Keney Park and Loomis Chaffee School.

Kitchen

Air conditioning

Family Stays: Middletown, CT

Middletown CT

$203 nightly

$230 total

Dec 15 - Dec 16

Total with taxes and fees

With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of Kidcity Children's Museum and General Mansfield House.

Kitchen

Washer

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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.