Pet-friendly holiday rentals in Winchester

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Popular amenities for Winchester pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Sewanee
4.94 out of 5 average rating, 96 reviews

The Sewanee House: Serene Oasis near Campus

FordRating, 5 stars2 weeks ago
Wonderful spot just off the downtown area of Sewanee. We enjoyed all the space and everyone in our group was able to get their own bed! The sunroom to the back yard is super relaxing and was a great hang out spot for our gang. Plenty of baby / toddler tools that are there for your use. This place spot is perfect for any Sewanee adventures!
Superhost
Home in Monteagle
4.87 out of 5 average rating, 23 reviews

Hickory Creek @ Trailhead Cabins

SueRating, 5 stars3 weeks ago
We were traveling long distance and needed something relaxing not far from the highway. I wish we’d had time to stay longer at this delightful cabin! This was everything we needed, dog friendly, clean and cozy. I especially enjoyed the large screened porch out back! I enthusiastically recommend this place!
Top guest favourite
Home in Tracy City
4.99 out of 5 average rating, 86 reviews

Little Green Cottage

MiaRating, 5 stars1 week ago
Perfect place to stay for a concert at the caverns! Peaceful and beautiful!
Guest favourite
Home in Sewanee
4.91 out of 5 average rating, 184 reviews

Return Guest House and Writers’ Retreat

SandraRating, 5 stars3 weeks ago
This is a lovely, peaceful place. Our group was two adult couples. We had a couple of birders and they were excited about the visit. We all enjoyed being close to Sewanee, local restaurants, and Mooney's Emporium.
Guest favourite
Home in Tracy City
4.95 out of 5 average rating, 21 reviews

Stay ON a Waterfall—13 acres! Bluffs, deck, views!

MarkRating, 5 stars1 month ago
Excellent host and home! Absolutely beautiful inside and out! My main love was the swinging bed! 2 nights spent and it was the best sleep ever!! Only thing I wish this property had was a hottub! The back decks are incredible, they would be even better with a hottub. Overall, a 5 out of 5 stars!!
Guest favourite
Home in Beersheba Springs
4.9 out of 5 average rating, 123 reviews

Modern Space in the Heart of Beersheba Springs

StephanieRating, 5 stars8 months ago
Amanda was super kind, responsive, and friendly. The place was full of character. Exactly the kind of place we wanted.
Top guest favourite
Home in Winchester
5 out of 5 average rating, 15 reviews

Lakeside Serenity: Cove Retreat

ElaineRating, 5 stars1 week ago
I felt like a welcomed guest from the minute I walked in. The home was spotless and smelled so clean and fresh. I have rented in Tennessee for the last 15 summers and have never rented a place that had so many extras (smores-popcorn- coffee pods-toiletries-kitchen supplies-etc. .Phil checked in to make sure everything was O:K. It is an absolute 5 Star !!!!
Guest favourite
Home in Whitwell
4.91 out of 5 average rating, 120 reviews

Blue Heron Lake House

JanetteRating, 5 stars3 weeks ago
Spectacular views! The house has everything you'll need either for a romantic getaway or a family gathering. Quick response from the owners regarding booking and normal house maintance issues. The charming home decor gives the house a relaxing vibe and the kitchen has everything you'll need to cook for a big family BBQ or a romantic dinner for two. We had a great experience, would definitely recommend!

Pet-friendly home rentals with a pool

Superhost
Home in Winchester
5 out of 5 average rating, 3 reviews

Barefoot Breeze

AustinRating, 5 stars1 week ago
Beautiful place we enjoyed our stay would love to come back if we are back in town.
Guest favourite
Home in Winchester
5 out of 5 average rating, 9 reviews

Twin Creeks Getaway, Pet Friendly!

CharlotteRating, 5 stars1 month ago
We have stayed here twice and it was great both times. We feel right at home. We love sitting on the front upstairs porch in the mornings and evenings. The inside is very nice and comfortable and has everything we need. It's a great location to walk down to the marina for lunch or dinner and to rent a boat. However, it is far enough away that you don't feel crowded by the busyness of the marina.
Top guest favourite
Cabin in Dunlap
4.98 out of 5 average rating, 105 reviews

Heaven’s View Lodge, Pool, Pet Friendly

LindaRating, 5 stars1 week ago
Heaven’s View Lodge is a beautiful cabin. The views are absolutely stunning. The cabin is well stocked, clean, modern and beautiful. The pool and hot tub were a wonderful addition, as was the fire pit. Nicely accommodates multi families traveling together. It was conveniently close to town but felt remote and private which was great. The hosts were wonderful. Definitely would recommend a stay at Heaven’s View!
Guest favourite
Home in Gruetli-Laager
4.95 out of 5 average rating, 20 reviews

Pool, Huge Backyard - Near Hiking & The Caverns

CariRating, 5 stars5 months ago
House was beautiful! Kevin was super accommodating & quick in responding to any questions we had. Would definitely recommend!
Top guest favourite
Cabin in Sewanee
5 out of 5 average rating, 40 reviews

Bougie Moms Cabin! Hot Tub|Sauna|Theatre

MelissaRating, 5 stars1 month ago
We loved our time at the Bougie Mom’s Cabin! Rachel and Steph really thought of everything! The beds were super comfy. The coffee bars with snacks were such a nice touch. We also loved the set up. Our families separate container homes for when they wanted privacy/quiet time. The swinging chairs on the patio of the tree house and the views were amazing! The swings were the grand-baby’s favorite! And so peaceful. We hated we could not stay longer. Next time we will stay longer.
Guest favourite
Home in Winchester
4.93 out of 5 average rating, 55 reviews

Basecamp Retreat TimsFordLake

SharonRating, 5 stars2 weeks ago
This home was beautiful and comfortable. Perfectly fitted with everything you need and more! The greened in back porch was heaven. The only tiny thing- I wish I had read closer bc while the house was on the lake, you don’t have direct access to walk to the water from the yard as I originally thought. By no means did it ruin the stay, that would have just made it absolutely perfect. Wonderful house, very easy to deal with and helpful owner, definitely recommend!!
Superhost
Home in Sewanee
4.79 out of 5 average rating, 19 reviews

Forest Retreat: Poolside Bliss Close to Campus

SamanthaRating, 5 stars1 month ago
A lovely stay, beautiful, peaceful, perfect
Top guest favourite
Home in Winchester
5 out of 5 average rating, 23 reviews

The Modern Mainstay at Barefoot Bay

MichaelRating, 5 stars5 days ago
Korina was very kind and responsive we absolutely loved to stay their and would definitely stay again!

Private, pet-friendly home rentals

Top guest favourite
Home in Tullahoma
5 out of 5 average rating, 94 reviews

Lakeside Retreat at The Reserve w/ Golf Cart

RandiRating, 5 stars1 week ago
Mathew’s place was perfect for our stay for my grandfather’s 83rd birthday. The house is so comfortable and has everything you could ever need. The back porch was a favorite spot for morning coffee and evening drinks. Everything was perfect!
Guest favourite
Cabin in Sequatchie
4.96 out of 5 average rating, 71 reviews

Fireside Cabin on the Bluff

RobbyRating, 5 stars1 month ago
Fiancé an I wanted a private get away, had eveything we needed, amazing view, nice to wake up to the birds chirping.
Top guest favourite
Cottage in Kelso
5 out of 5 average rating, 24 reviews

Clementine Cottage

DarleneRating, 5 stars10 months ago
The Clementine Cottage was perfect. It was cute, quaint, CLEAN, well outfitted with lots of nice extras. She had brochures on all the nearby activities. We fished, we kayaked, we sat around the fire pit, we enjoyed the screened porch. My only complaint would be that I mistakenly thought the cabin would be a little more secluded but even with that being said, it was quiet, it was serene, we enjoyed our long weekend very much and are talking about another trip there. And Gloria is a great hostess. We were pleasantly surprised at how nice everything was.
Guest favourite
Cottage in Tracy City
4.97 out of 5 average rating, 58 reviews

Swordfish Suite - Pup Shed Retreat

JeffRating, 5 stars1 week ago
Awesome place with tons of great outdoor activities. Nice community with good public spaces. Comfy beds, great ac, easy access to amenities. Pup shed was a great additional space. Host very prompt to communicate as well. Would definitely stay again!
Top guest favourite
Home in Tullahoma
4.98 out of 5 average rating, 60 reviews

Beautiful cottage next to Tims Ford Lake

LaurelRating, 5 stars5 days ago
Matt was very sweet and gave us many helpful tips during our stay! I would 100% recommend this place to anyone who is trying to have a peaceful and laidback vacation!
Top guest favourite
Home in Winchester
5 out of 5 average rating, 30 reviews

On Water w/ Private Dock, Entire Home, sleeps 14

NatalieRating, 5 stars1 week ago
We loved our stay! The house was clean and exactly as described. Chris was extremely responsive and I appreciated he offered an early check in without us even asking! It is in a neighborhood but felt extremely private. The dock is very private. I especially loved how close we were to twin lakes marina both by car and boat. We would absolutely stay again!
Guest favourite
Guest house in Sewanee
4.91 out of 5 average rating, 56 reviews

Little Bird Cottage

SusanRating, 5 stars2 weeks ago
It was the perfect place and we loved it! Very well kept and had everything we needed. Beautiful setting with lake out the back door! It was on campus and a short distance from all that we needed! I highly recommend Lindsey and her cottage!
Top guest favourite
Townhouse in Winchester
5 out of 5 average rating, 18 reviews

AquaHallics Retreat 2

MistyRating, 5 stars5 days ago
This place was great! It was beautiful and clean. Had everything you needed for your stay. We had a last minute booking and a bad situation with another place and they were able to get us right in. We really appreciate the hospitality and hope to be back again.

Quick stats about holiday rentals that are pet-friendly in Winchester

  • Total rentals

    30 properties

  • Nightly prices starting at

    $77 SGD before taxes and fees

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore