Cottage vacation rentals in Middlesex County
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Middlesex County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Middlesex County cottage rentals
Cottage rentals with a hot tub
Cottage in Old Lyme
4.8 out of 5 average rating, 172 reviewsPrivate Beach Cottage
Jun 22 – 29
Cottage in Cutchogue
4.69 out of 5 average rating, 187 reviewsLovely 2 BR Beach House No. Shore
Apr 29 – May 6
Cottage in Southampton
4.96 out of 5 average rating, 164 reviewsSecluded Southampton Cottage w/Pool & Spa
Jan 25 – Feb 1
Cottage in Burlington
5.0 out of 5 average rating, 44 reviewsCozy Cottage w/Lakefront Views, Swim Spa & Firepit
Nov 27 – Dec 4
Cottage in Eastford
4.89 out of 5 average rating, 75 reviewsSerenity Ashford Lake
Aug 8 – 15
Cottage in Southampton
4.85 out of 5 average rating, 13 reviewsSPA DEPARTURES NEAR THE SEA
Nov 21 – 28
Cottage in Coventry
4.82 out of 5 average rating, 17 reviewsLakefront Connecticut Retreat Near UConn
Jun 29 – Jul 6
Cottage in East Hampton
4.89 out of 5 average rating, 19 reviewsEast Hampton Springs - Private Beach Getaway
Mar 27 – Apr 3
Pet-friendly cottage rentals
Cottage in East Haddam
4.93 out of 5 average rating, 86 reviewsCottage on the hill
Jun 27 – Jul 4
Cottage in Westbrook
4.85 out of 5 average rating, 98 reviewsPeaceful Riverfront Cottage w/Dock, Walk to Beach
Cottage in Old Saybrook
4.95 out of 5 average rating, 44 reviews1920’s charming dollhouse near South Cove
Apr 21 – 28
Cottage in Essex
4.93 out of 5 average rating, 30 reviewsEssex House
Jan 3 – 10
Cottage in East Hampton
4.84 out of 5 average rating, 25 reviewsCharming 3 bedroom cottage on Lake Pocotopaug
Apr 5 – 12
Cottage in Guilford
5.0 out of 5 average rating, 15 reviewsWaterfront Cottage With Unforgettable Views
Feb 3 – 10
Cottage in Guilford
4.96 out of 5 average rating, 70 reviewsDirect Shoreline Long Island Sound Waterfront
Jan 6 – 13
Cottage in Clinton
4.96 out of 5 average rating, 24 reviewsSeaside Twinhome Retreat: 2 Private Sides+Sunroom!
Mar 31 – Apr 7
Private cottage rentals
Cottage in Westbrook
4.99 out of 5 average rating, 80 reviewsThe Old Salt Cottage · Cozy Gateway Near Beach
Jan 24 – 31
Cottage in Guilford
5.0 out of 5 average rating, 82 reviewsWaterfront Joshua Cove Cottage with private beach.
May 27 – Jun 1
Cottage in Old Saybrook
4.97 out of 5 average rating, 75 reviewsBeautiful Cottage View
Jan 26 – Feb 2
Cottage in Westbrook
4.98 out of 5 average rating, 55 reviewsBeautiful Updated Cottage walk to the Beach
Sep 8 – 15
Cottage in Lebanon
4.98 out of 5 average rating, 47 reviewsPeek-A-Boo View, Amston Lake
Apr 24 – May 1
Cottage in Middlefield
5.0 out of 5 average rating, 82 reviewsAnchors' Away-
Oct 1 – 8
Cottage in Essex
4.94 out of 5 average rating, 36 reviewsCheerful, private cottage in Essex village.
Jan 26 – Feb 2
Cottage in Westbrook
4.91 out of 5 average rating, 68 reviewsA Beach House Gem
Mar 31 – Apr 7
Destinations to explore
- Cottage rentals Connecticut
- Kid-friendly rentals Middlesex County
- Fitness-friendly rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with lake access Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with breakfast Middlesex County
- Rentals with a fire pit Middlesex County
- Monthly Rentals Middlesex County
- Pet-friendly rentals Middlesex County
- House rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Beachfront rentals Middlesex County
- Rentals with pools Middlesex County
- Rentals with a washer and dryer Middlesex County
- Private suite rentals Middlesex County
- Family-friendly rentals Middlesex County
- Bed and breakfasts Middlesex County
- Guesthouse rentals Middlesex County
- Apartment rentals Middlesex County
- Rentals with a hot tub Middlesex County
- Rentals with an EV charger Middlesex County
- Waterfront rentals Middlesex County
- Rentals with a patio Middlesex County
- Rentals with beach access Middlesex County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom