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Apartment vacation rentals in Middlesex County

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Top-rated apartment rentals in Middlesex County

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Rental unit in East Haddam

4.78 out of 5 average rating, 271 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Rental unit in Old Lyme

4.89 out of 5 average rating, 195 reviews

Private apartment in historic Old Lyme mansion

3rd floor apartment in Ludington House, a historic home centrally located in the charming village of Old Lyme. 3 bedrooms (2 queen, and one with two twin beds/trundle), 2 full bathrooms. Close to restaurants, beaches, art galleries and museum. Please do not book for a group that does not include yourself. Person booking the apartment must be one of the guests staying. COVID update: At this time we cannot allow guests that are not part of the reservation to visit the property during your stay.

Rental unit in Chester

4.93 out of 5 average rating, 343 reviews

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

ONE night stays are available for last minute bookings, message us! If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled livingroom w/high ceilings, quiet, private bedroom in back, and w/large private deck overlooking Pattaconk Brook. A true gem, set up solely 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!!!

Rental unit in Middletown

4.94 out of 5 average rating, 750 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.

Rental unit in Guilford

4.99 out of 5 average rating, 269 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Rental unit in Glastonbury

4.9 out of 5 average rating, 419 reviews

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

Rental unit in Chester

4.98 out of 5 average rating, 152 reviews

Charming Chester Retreat-Hidden Gem

This thoughtfully designed 2 bed, 1 bath unit is the perfect blend of style and comfort. The space has been re-designed to feature a modern kitchen, soaking tub and wood-burning fireplace. The unit also features a roof deck that overlooks our mature maple trees and a sprawling front porch, complete with rockers. Great for 1-2 couples, small families or group of friends—Ask about our single roll away bed or pack' n' play(s). Kid friendly! New England getaway / Hidden Gem / Retreat

Rental unit in Deep River

4.92 out of 5 average rating, 132 reviews

Lovely Garden-Level Apartment in Heart of Town

This garden-level apartment is centrally located within walking distance to Main Street's retail shops, restaurants, and grocery/pharmacy, and just minutes from The Lace Factory and Deep River Landing, Essex Steam Train & Riverboat, Connecticut River Museum, the CT shoreline and beaches, and so much more. A charming historic home over 200 years old with a classic New England feel, the apartment has two bedrooms, one full bath, and an eat-in kitchen complete with amenities.

Rental unit in Old Saybrook

4.97 out of 5 average rating, 119 reviews

Convenient and Cute in Downtown Old Saybrook

Welcome to Old Saybrook! Our apartment sits over our garage and is attached to our primary residence. It is conveniently located within walking distance to Main Street, the beach, local parks, and other town attractions. We have recently made many upgrades to the property and we're ready for guests! We look forward to sharing our home with you! **PETS: DOGS ALLOWED BY PRE-APPROVAL ONLY and ADDITIONAL $25 PET CLEANING FEE. Please see House Rules for more info.

Rental unit in East Haddam

4.9 out of 5 average rating, 149 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Rental unit in Branford

4.97 out of 5 average rating, 103 reviews

Ridgeview Suite at Stony Creek Depot

The New England-chic interior design of the 1,300-sf Ridgeview Suite blends modern amenities with charming, unique vintage artifacts. With a large bright kitchen, office/library, wet-bar and laundry room, this 2-bedroom suite is ideal for families or corporate guests. Savor small town life in Stony Creek Village with its small public beach, playground, and sandwiches shops in town.

Rental unit in Middletown

4.93 out of 5 average rating, 100 reviews

Private Downtown Oasis

Private First Floor Rear Apartment of an 1849 historical home in the heart of Middletown, CT. One block walk to Wesleyan University with private parking. Main street also one block away with many great restaurants, and our best local coffee shop (Klekolo) just doors away from your apartment. The House is across from the public library. Stone patio in a lovely fenced in rear yard.

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Popular amenities for Middlesex County apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Rental unit in East Haddam

5 out of 5 average rating, 3 reviews

The Chace Suite

Rental unit in Killingworth

5 out of 5 average rating, 5 reviews

CT Countryside/Shoreline Retreat

Rental unit in Westbrook

4.89 out of 5 average rating, 9 reviews

Meadowview & Pondside Retreat

Rental unit in Madison

Shoreline Casita

Rental unit in Middletown

New place to stay

Vegan Artist's Retreat

Rental unit in Chester

5 out of 5 average rating, 7 reviews

The Little Chestnut.

Rental unit in Middletown

4.59 out of 5 average rating, 88 reviews

Private Apartment III Near Wesleyan University

Rental unit in Madison

4.89 out of 5 average rating, 19 reviews

42 Wall - The Heart of Madison

Private apartment rentals

Rental unit in Chester

5 out of 5 average rating, 14 reviews

New, modern studio steps from downtown Chester CT

Rental unit in Clinton

4.97 out of 5 average rating, 35 reviews

Shoreline Oasis

Rental unit in Killingworth

4.93 out of 5 average rating, 29 reviews

Life on the Farm

Rental unit in Westbrook

5 out of 5 average rating, 5 reviews

Private Guest Suite Water Views

Rental unit in Guilford

4.96 out of 5 average rating, 55 reviews

Cozy Private Lake Q Retreat

Rental unit in Chester

4.89 out of 5 average rating, 55 reviews

Gingerbread Apartment, Walk Downtown

Rental unit in Chester

4.99 out of 5 average rating, 86 reviews

The Millhouse Downtown Chester

Rental unit in Clinton

4.98 out of 5 average rating, 66 reviews

Cozy Shoreline Getaway

Apartment rentals with a hot tub

Rental unit in New Haven

4.75 out of 5 average rating, 138 reviews

Luxury Penthouse Minutes to Yale

Rental unit in Southampton

5 out of 5 average rating, 78 reviews

Private w/Hot tub Fire Pit Coffee Bar

Rental unit in Norwich

4.65 out of 5 average rating, 23 reviews

Cozy spa condo with pools near Mystic/Mohegan Sun

Rental unit in Montville

4.81 out of 5 average rating, 101 reviews

Cozy Studio: Indoor Hot Tub & Inground Pool Access

Rental unit in Waterford

5 out of 5 average rating, 22 reviews

Garden Suite: Private, Near Mohegan Sun & USCGA

Rental unit in Norwich

4.92 out of 5 average rating, 12 reviews

Chalet Tré

Rental unit in Norwich

4.88 out of 5 average rating, 8 reviews

Retreat at Norwich Inn and Spa

Rental unit in New Haven

4.67 out of 5 average rating, 3 reviews

Newly Renovated 2 bedroom Apartment close to Yale

Destinations to explore