Holiday rentals in Haddam

4.79 out of 5 average rating, 284 reviews

Flat in East Haddam

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.

4.93 out of 5 average rating, 371 reviews

Flat in Chester

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!!!

4.94 out of 5 average rating, 803 reviews

Flat in Middletown

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.

4.95 out of 5 average rating, 221 reviews

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

4.97 out of 5 average rating, 273 reviews

Cottage in Chester

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

4.97 out of 5 average rating, 29 reviews

Home in Haddam

The Farmhouse Stay

Designed to be your very own home away from home. At The Farmhouse Stay, we’ve honored its history and all that makes it special, while thoughtfully tucking in modern additions to create a cozy, contemporary environment for today’s houseguest. The Farmhouse Stay is a 1780 cape situated on 15 quiet acres. The 2,000 square ft home features 2 bedrooms, 2 bathrooms, an eat-in kitchen, butler’s pantry, living room, formal dining room, dedicated laundry room, and an upper level landing.

5 out of 5 average rating, 200 reviews

Guest house in Portland

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

5 out of 5 average rating, 126 reviews

Home in Haddam

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

4.99 out of 5 average rating, 142 reviews

Loft in Chester

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK

Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

5 out of 5 average rating, 22 reviews

Home in Higganum

The Doll House

Enjoy the Connecticut River Valley at this cozy retreat close to where you want to be. Conveniently located near Route 9, the Doll House is easy to get to from Middletown, the shoreline, and Central CT. Enjoy the patio while having dinner or just taking in the outdoors. Take advantage of all the area has to offer, from hiking, to shows at the Goodspeed Opera House, and fine dining options in Downtown Middletown. Enjoy this private setting surrounded by nature.

4.9 out of 5 average rating, 168 reviews

Flat in East Haddam

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.

4.72 out of 5 average rating, 241 reviews

Cottage in Deep River

Cottage overlooking the CT river

Adorable 1800 cottage with views of the CT River. Upstairs bedroom with a king. Bathroom downstairs with a small tub / shower and a tiny kitchen. Other room is a living room with a desk/ table but has a queen pull out bed ( needs to be requested ahead of time. Watch the Essex steam train, Becky Thatcher riverboat, or hang out at the river, bring your kayaks or paddleboards as there is a boat ramp right across the street.

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Other great holiday rentals in Haddam

5 out of 5 average rating, 5 reviews

Guest suite in Clinton

Private 2-room suite + bath in beach town

LizzieRating, 5 stars2 weeks ago

We had a great time! The unit is very clean and comfortable and has everything you would need. The unit is exactly as pictured and described. The outdoor amenities (hot tub, deck and grill) are a huge bonus. The outdoor space is so calm and serene. The neighborhood is very quiet and peaceful and there are plenty of food/dining options within driving distance in lieu of a full kitchen (which is already described). Delicious lobster rolls are only a few minutes away via car which is great! While we were there we visited Lake Compounce as well as the USS Nautilus - that was fun! Suzanne is such a kind and wonderful host. She made our stay extra pleasant and was always available to answer questions or provide anything necessary. She provided a snack basket which came in handy and was much appreciated. Her dog,Molly, is a sweet dog and we enjoyed her company. We are so grateful for Suzanne and her warm hospitality :) Thank you once again!

5 out of 5 average rating, 8 reviews

Home in Haddam

Quarry House: Mid-Century Modern

RobertRating, 5 stars1 week ago

We enjoyed a lovely long weekend getaway at Quarry House. The house is better than the photos, so thoughtfully designed and decorated, and very clean. We appreciated the high quality toiletries, towels and bedding, as well as the clean, high quality appliances and well-stocked kitchen. The property was quiet and we spent time enjoying the deck. The host was very responsive to the few questions and needs we had while staying there.( If you're a book lover, take a trip over to Niantic to visit The Book Barn!)

4.81 out of 5 average rating, 52 reviews

Flat in Middletown

Cozy Apartment Near Wesleyan and Town Center

RyanRating, 5 stars1 week ago

Great place I felt at home from the moment I stepped inside The place was very very clean and had everything for a long stay. The location was close by to everything

4.97 out of 5 average rating, 35 reviews

Flat in Middletown

Your Sweet Spot in Middletown CT

JessicaRating, 5 stars1 month ago

My husband and I enjoyed our stay at the Sweet Spot. It’s a cozy studio in-law apartment built off the main home. The apartment was clean and well kept. We had the pleasure of meeting our host, Bridget, and she shared that they had recently converted the space from a sun room into an apartment. We didn’t have the opportunity to meet Collette. Location is prime as it’s close to downtown Middletown, Wesleyan University, as well as easy access to Route 9. Being close to Main St. made it easy for us to get up in the morning and grab a quick breakfast before heading out for the day. The neighborhood they are in is peaceful, located in a residential area. Would book again.

Guest house in Middletown

5 out of 5 average rating, 5 reviews

Cozy Historic Home Guest Suite

RandyRating, 5 stars2 days ago

Beautiful old school house with amazing furniture. great! comfy bed. perfect bathroom. wonderful porch. couldn't recommend more 10 out of 10. very accommodating and allowing me to record the last episode of my podcast. really appreciate this host

4.81 out of 5 average rating, 21 reviews

Flat in Clinton

Bright & Cozy Loft Near Beach

ErickaRating, 5 stars1 week ago

Diana's place was an absolute joy to stay in. The serene surroundings were just beautiful. So quiet and the perfect getaway to unplug. Lots of local restaurants to choose from as well! Highly recommended staying here!

5 out of 5 average rating, 18 reviews

Cabin in East Haddam

Lakeshore Cabin with boat dock

IrenaRating, 5 stars3 weeks ago

We spent a long weekend at Dennis’ place and it was nothing short of amazing. Our aim was to relax and enjoy the lake, and we did just that. The house was exactly as described, matched and exceeded our expectations; furnished and the kitchen had everything we needed and more. If we’re back in CT, we won’t hesitate to book the house again! Thanks for being wonderful hosts!