Vacation rentals in Middlesex County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middlesex County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Sep 28 – Oct 5

$296 per night
Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 309 reviews

Chester Village 'Pied-à-terre' above art gallery

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT! NEW! Winter weekdays - ONE night stays are now available - message us!

Dec 20 – 27

$177 per night
Guest favorite

Apartment in Middletown

4.94 out of 5 average rating, 695 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

Dec 6 – 13

$106 per night

Popular amenities for Middlesex County vacation rentals

Other great vacation rentals in Middlesex County

Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 228 reviews

Lake Beseck cottage

Feb 1 – 8

$150 per night
Guest favorite

Home in Chester

4.98 out of 5 average rating, 194 reviews

Stunning Artisan Waterfall Escape, Walk Downtown

May 3 – 10

$286 per night
Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 48 reviews

Cozy Shoreline Getaway

May 25 – Jun 1

$105 per night
Guest favorite

Home in Haddam

5.0 out of 5 average rating, 69 reviews

Cozy Comforts!

Jun 28 – Jul 5

$129 per night
Guest favorite

Apartment in Guilford

4.88 out of 5 average rating, 17 reviews

Cozy Private Lake Q Retreat

Jan 3 – 10

$134 per night
Guest favorite

Guest suite in Durham

4.83 out of 5 average rating, 18 reviews

Spacious Studio in quiet neighborhood.

Jul 24 – 31

$95 per night
Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 58 reviews

Lovely one bedroom studio with on-site parking.

May 16 – 23

$125 per night
Guest favorite

Guesthouse in Madison

5.0 out of 5 average rating, 57 reviews

The Barn by the Sound

Apr 23 – 30

$144 per night
Guest favorite

Guesthouse in Portland

5.0 out of 5 average rating, 58 reviews

Guesthouse Farm Stay

Sep 2 – 9

$131 per night
Guest favorite

Condo in Middletown

4.97 out of 5 average rating, 99 reviews

Entire place to yourself Cromwell/Middletown Line

Oct 24 – 31

$104 per night
Guest favorite

Loft in Chester

4.99 out of 5 average rating, 82 reviews

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Apr 25 – May 2

$156 per night
Guest favorite

Cottage in East Haddam

5.0 out of 5 average rating, 39 reviews

Cheerful updated cottage in Lake Hayward Community

Feb 9 – 16

$113 per night

Destinations to explore