8 ‘Gilmore Girls’-Coded Airbnbs That Will Make You Feel Like You’re Vacationing in Stars Hollow

Including a stay in the town that inspired the show

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While many people love to rewatch Gilmore Girls at the start of fall, thanks to the show’s cozy small-town setting, I rewatch it over and over (and over) again year-round, so I feel especially qualified on the subject. And if you were hoping to take a trip inspired by the nostalgic show this season—or any other time of year—you’re in luck, because I vetted dozens of Airbnb listings to find eight stays with serious Stars Hollow vibes. Find farmhouses, cottages and other unique homes in locations like Hartford, New Haven, and Martha’s Vineyard below.

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1. Farmhouse Stay (Milford, CT)

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  • Bedrooms and Bathrooms: 2 bedrooms, 2.5 bathrooms
  • Rate: from $354/night
  • Why We Love It: cozy stone fireplace, spacious front porch, situated on a working farm that guests can explore, laundry
  • Pet-Friendly: no

The porch that spans the front of Lorelai’s home is one of the most iconic things from the show, so naturally, this farmhouse stay in Milford, Connecticut, with a similar one caught my attention. It also has a stone fireplace that gives it a homey, cozy vibe and, while very different from the small walkable town we all know and love, this one’s actually situated on a working farm that you’ll be able to explore—a bonus, if you ask me. One recent guest said: “The farm itself is well-kept, with lots of furry friends to visit, and the farmhouse is clean and cozy with beautiful details. Lots to do locally as well!”

  • Bedrooms and Bathrooms: 5 bedrooms, 2 bathrooms
  • Rate: from $439/night
  • Why We Love It: historic home, professionally decorated, glamping shed, heated lagoon pool, laundry, fireplace
  • Pet-Friendly: yes

The second I spotted this home, I thought it looked like something Emily Gilmore herself could have designed. Turns out, it was professionally decorated to give it its elevated style. The patterned sofa looks perfect for curling up with a pre-Friday night dinner drink, and then before you’re ready to call it a day, you can take a dip in the heated lagoon pool. The home itself is historic, having been first built in 1790, but you can expect tons of modern amenities. One guest raved that “the home is beautiful, as are the surrounding areas,” and said it was “stunningly decorated and yet also surprisingly toddler-safe and kid-friendly.”

3. Island Beach Rose (Oak Bluffs, MA)

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  • Bedrooms and Bathrooms: 4 bedrooms, 2 bathrooms
  • Rate: from $985/night
  • Why We Love It: 1870s Victorian home, can walk to the beach and local stores and restaurants, wrap-around porch, patio, in a town with a gazebo, laundry
  • Pet-Friendly: yes

Featuring another spacious wrap-around porch, this home could pass as an inn like the Independence or Dragonfly. It has an 1870s Victorian style on the outside, but the inside looks much more modern with a coastal vibe that’s ideal for its location, considering you can walk to the beach and local shops. Speaking of things nearby, there’s a gazebo pictured in the center of a nearby square, so you can imagine you walked right into the center of Stars Hollow. “A beautiful and comfortable cottage in a wonderful location for Oak Bluffs downtown and beach access. Amazing porch and peaceful back patio,” shared one reviewer.

  • Bedrooms and Bathrooms: 1 bedroom, 1 bathroom
  • Rate: from $138/night
  • Why We Love It: historic Hartford neighborhood, featured on HGTV, colorful decor, shared deck
  • Pet-Friendly: no

This loft in Hartford has a colorful, fun interior design that I could totally picture Lorelai loving—and she wouldn’t be the only one, considering this stay has been featured on HGTV. It’s situated in a historic neighborhood where you’ll be able to find plenty of restaurants, art exhibits and live theater, and one recent guest said the space felt “homey and comfortable” and had “everything [they] could have needed.” (Just note that this one is located up three flights of shared stairs and there is no door separating the loft from the stairway, but the hosts ensure having privacy won’t be an issue.)

  • Bedrooms and Bathrooms: 3 bedrooms, 2.5 bathrooms
  • Rate: from $291/night
  • Why We Love It: close to Yale, patio with fire pit, spacious backyard, walkable neighborhood, laundry
  • Pet-Friendly: no

If you prefer the Rory-at-Yale seasons, you might want to opt for this stay in New Haven that’s near the campus. The private back patio reminds me of the one at Richard and Emily’s home where they would often host guests, and it also includes access to a spacious backyard. There’s plenty of space for sleeping, too, including trundle beds that I could picture Rory and Lane using for a sleepover in their high school years. “The home was warm, super inviting, and had such a cozy, personal touch,” said a guest.

6. Martha’s Vineyard Cottage (Edgartown, MA)

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  • Bedrooms and Bathrooms: 4 bedrooms, 3 bathrooms
  • Rate: from $923/night
  • Why We Love It: walkable to local stores, restaurants and beach, 1920s cottage, skylights, patio, laundry, fireplace
  • Pet-Friendly: yes

If you’ve been dreaming of staying on Martha’s Vineyard ever since watching the episode where Logan brings Rory, Lorelai and Luke to his family’s vacation home, you might consider splurging on a stay at this 1920s cottage. You could easily bring your own group, too, since it’s equipped with four bedrooms that can accommodate up to nine guests. You’ll love its location, which is walkably close to local stores and restaurants and the beach, but be sure to take advantage of the sun-filled dining space, too. One reviewer who stayed over the Fourth of July said: “The house is in a great location, which made coffee runs and dinners so convenient during a really busy time. We had our two dogs, which made the fenced-in yard a top amenity.”

7. Litchfield Hills Country Hideaway (Washington, CT)

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  • Bedrooms and Bathrooms: 2 bedrooms, 1 bathroom
  • Rate: from $616/night
  • Why We Love It: located in the town that inspired Stars Hollow, nearby trail, laundry, patio, shared backyard
  • Pet-Friendly: yes (dogs only)

Did you know that the town of Washington, Connecticut, was actually the inspiration for Stars Hollow?  Well, now you do, and you can stay at this cozy cottage to see it for yourself. The whole space has a vibe that manages to balance feeling homey and modern in the best way. With a trail entrance right on the property, you can start your day with a nature walk or go for a mid-afternoon stroll (which has to be stunning in the fall, in particular, as the leaves change).  “What an amazing stay! The house was beautifully decorated and set in gorgeous surroundings. Every detail felt thoughtfully put together,” raved a reviewer.

  • Bedrooms and Bathrooms: 1 bedroom, 1 bathroom
  • Rate: from $230/night
  • Why We Love It: authentic 1906 SOO-Line caboose, situated on a working farm, close to trails, shops and wineries, fireplace, deck
  • Pet-Friendly: no

While it may not be your first thought for a Gilmore Girls-inspired stay, when I saw this unique railcar listing, I couldn’t help but think that it looks just like the fun, quirky type of thing I could see Taylor Dosey trying to install in the Stars Hollow town square. It’s situated on a working farm, and despite its small size, it still features a fireplace, deck, kitchenette and more. It has exclusively earned five-star ratings, and one guest said: “The renovation of the caboose is absolutely incredible and beautifully designed. The character of the train is retained yet was so comfortable with thoughtful touches in every little nook. It was also nice to be able to eat outside on the porch and visit the horses.”


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Natalie LaBarbera

Contributing Editor, Commerce

  • Writes commerce stories and features that span multiple topics, including fashion, beauty, travel, home and sales/deals
  • Has contributed to reports on ethical fashion and continues to stay up-to-date on sustainablility developments
  • Completed a bachelor's degree in psychology at the University of Pittsburgh and a master's degree in fashion studies at Parsons The New School