Holiday rentals in Connecticut

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Top-rated holiday rentals in Connecticut

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

Guest favourite
Flat in Milford
Water front studio apartment with fireplace.
This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!
28 Aug – 4 SepIndividual Host,
€ 218 per night
4.97 out of 5 average rating, 505 reviews
Guest favourite
Guest house in Stonington
True Artist Loft, 5 minutes to downtown Mystic
The Dacha, as it has lovingly been called for almost 80 years was built in 1945 originally as a studio for the artist that resided on the property. The unique structure is truly one of a kind, fully insulated for winter and tucked away from the road, sitting on a quiet piece of land, just 5 minutes to downtown Mystic. Enjoy modern comforts and a designers decor, while settling in front of the fire, or taking a short drive to all that Mystic has to offer- hiking, water, shops and restaurants.
22–29 AugIndividual Host,
€ 253 per night
4.98 out of 5 average rating, 216 reviews
Guest favourite
Guest suite in Wallingford
Wintergreen Gardens Suite @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.
8–15 JanIndividual Host,
€ 87 per night
5.0 out of 5 average rating, 492 reviews

Popular amenities for Connecticut holiday rentals

Other great holiday rentals in Connecticut

Guest favourite
Guest house in Mystic
Gorgeous Waterfront Getaway
28 Nov – 3 DecIndividual Host,
€ 205 per night
4.99 out of 5 average rating, 536 reviews
Guest favourite
Cottage in East Lyme
Your Nest Near The Beach
22–29 MayIndividual Host,
€ 268 per night
4.97 out of 5 average rating, 232 reviews
Guest favourite
Home in Stamford
Midcentury Modern ZenHouse Sculptor Studio
31 Aug – 7 SepIndividual Host,
€ 601 per night
4.97 out of 5 average rating, 216 reviews
Guest favourite
Home in East Haven
The Breakaway - a waterfront gem.
4–11 SepIndividual Host,
€ 310 per night
4.94 out of 5 average rating, 88 reviews
Guest favourite
Home in East Haddam
Romantic Getaway at The Lake!
23–30 AugIndividual Host,
€ 242 per night
4.95 out of 5 average rating, 84 reviews
Guest favourite
Home in Haddam
Cozy Comforts!
12–19 NovIndividual Host,
€ 135 per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Tiny home in East Lyme
Lakefront Boho Tiny House
23–30 MayProfessional Host,
€ 288 per night
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Milford
Direct Oceanfront Home
30 Oct – 6 NovIndividual Host,
€ 513 per night
5.0 out of 5 average rating, 37 reviews
Guest favourite
Cottage in Guilford
Waterfront Joshua Cove Cottage with private beach.
23–30 SepIndividual Host,
€ 514 per night
5.0 out of 5 average rating, 80 reviews
Guest favourite
Loft in Milford
Lovely water front lower-level loft, free parking
13–20 AugIndividual Host,
€ 139 per night
4.93 out of 5 average rating, 92 reviews
Guest favourite
Cabin in North Grosvenordale
Secluded cabin w/ Finnish Sauna & Forest Baths
2–9 SepIndividual Host,
€ 214 per night
5.0 out of 5 average rating, 49 reviews
Guest favourite
Cottage in Bethlehem
Wood Burning Fireplace |Soaking Tub |Pet Friendly
19–26 JulIndividual Host,
€ 211 per night
5.0 out of 5 average rating, 25 reviews

Destinations to explore