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.
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
Apartment in Chester
4.95 out of 5 average rating, 309 reviewsChester 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
Apartment in Middletown
4.94 out of 5 average rating, 695 reviewsQuaint 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
Vacation rentals for every style
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Popular amenities for Middlesex County vacation rentals
Other great vacation rentals in Middlesex County
Cottage in Middlefield
4.93 out of 5 average rating, 228 reviewsLake Beseck cottage
Feb 1 – 8
Home in Chester
4.98 out of 5 average rating, 194 reviewsStunning Artisan Waterfall Escape, Walk Downtown
May 3 – 10
Apartment in Clinton
4.98 out of 5 average rating, 48 reviewsCozy Shoreline Getaway
May 25 – Jun 1
Home in Haddam
5.0 out of 5 average rating, 69 reviewsCozy Comforts!
Jun 28 – Jul 5
Apartment in Guilford
4.88 out of 5 average rating, 17 reviewsCozy Private Lake Q Retreat
Jan 3 – 10
Guest suite in Durham
4.83 out of 5 average rating, 18 reviewsSpacious Studio in quiet neighborhood.
Jul 24 – 31
Loft in Westbrook
5.0 out of 5 average rating, 58 reviewsLovely one bedroom studio with on-site parking.
May 16 – 23
Guesthouse in Madison
5.0 out of 5 average rating, 57 reviewsThe Barn by the Sound
Apr 23 – 30
Guesthouse in Portland
5.0 out of 5 average rating, 58 reviewsGuesthouse Farm Stay
Sep 2 – 9
Condo in Middletown
4.97 out of 5 average rating, 99 reviewsEntire place to yourself Cromwell/Middletown Line
Oct 24 – 31
Loft in Chester
4.99 out of 5 average rating, 82 reviewsThe Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
Apr 25 – May 2
Cottage in East Haddam
5.0 out of 5 average rating, 39 reviewsCheerful updated cottage in Lake Hayward Community
Feb 9 – 16
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