Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

Guest favorite

Tiny home in Oxford

4.96 out of 5 average rating, 285 reviews

⭐Wildflower Country Cottage

🏡 Cozy cottage in the countryside. Gardens galore to explore! 🏘 Less than 5 minutes from town 🎟 Many local attractions including: 🦒 Animal Adventure 🏎 Northeast Classic Car Museum 🥾 State Parks, and hiking trails 🚶‍♂️Enjoy an afternoon in the gazebo or take a stroll around any of the many garden paths. 📕 See our guidebook for our favorite local attractions and eateries. ℹ️ Please check out our other listing: Lakeside Reflections https://airbnb.com/h/lakesidereflections

Aug 4 – 11

€ 126 per night
Guest favorite

Apartment in Oxford

4.98 out of 5 average rating, 567 reviews

Breezy Meadow

My place is close to Oxford and Norwich NY .You’ll love my place because of Country living at its finest pond,stream, 20 acres,nature trails spectacular views from every window. Brand new beautiful custom kitchen with stainless steal appliance. Spa like bathroom. There is also a small cottage on pond to relax in Great place to kick off shoes and really relax.. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends ((dogs) 1TIME $30 per dog

Jan 19 – 26

€ 99 per night
Guest favorite

Home in Binghamton

4.95 out of 5 average rating, 280 reviews

Quiet Private Apartment Park Setting West Side

This is an older home with one apartment on the first floor and a vacant apartment upstairs. Guests have the entire property to themselves. Free off-street parking. There is a small park across the street and a larger city park one block away w/carousel, pool, tennis courts, ice rink (all seasonal), amazing playground and walking paths. Three hospitals are within a 10 minute drive. Close to BU/SUNY. A nice variety of restaurants, bars, shops, antiques in the area. Check out the guidebook!

Nov 23 – 30

€ 131 per night

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Dollar General3 locals recommend
Big M4 locals recommend
China Star3 locals recommend

Other great vacation rentals in Windsor

Guest favorite

Home in Windsor

4.94 out of 5 average rating, 85 reviews

Welcome to Serenity. Country setting. All 1 floor.

Jul 17 – 24

€ 171 per night
Guest favorite

Chalet in Susquehanna

5.0 out of 5 average rating, 83 reviews

DEER RUN LODGE

May 18 – 25

€ 100 per night
Guest favorite

Home in Conklin

5.0 out of 5 average rating, 38 reviews

The river house

Jan 17 – 24

€ 221 per night
Guest favorite

Guest suite in Deposit

5.0 out of 5 average rating, 24 reviews

Cozy studio apartment above charming cafe

Oct 6 – 13

€ 122 per night
Guest favorite

Apartment in Binghamton

4.97 out of 5 average rating, 33 reviews

Modern 2-Bedroom Apt close to Downtown & Highway

Apr 25 – May 2

€ 107 per night
Guest favorite

Apartment in Bainbridge

4.96 out of 5 average rating, 84 reviews

Botanica Retreat

Oct 16 – 23

€ 113 per night
Guest favorite

Cabin in Guilford

5.0 out of 5 average rating, 34 reviews

Bear-ly Camping Gray Cabin

Jan 31 – Feb 7

€ 127 per night
Guest favorite

Guesthouse in Greene

4.98 out of 5 average rating, 43 reviews

Cozy, comfort in Greene, NY with beautiful view

Jul 5 – 12

€ 117 per night
Guest favorite

Apartment in Greene

4.97 out of 5 average rating, 72 reviews

Spacious apartment overlooking Greene NY

Oct 8 – 15

€ 105 per night
Guest favorite

Home in Bainbridge

4.96 out of 5 average rating, 72 reviews

"Peaceful Up-State GETAWAY on 66acres"

Jul 21 – 28

€ 122 per night
Guest favorite

Guesthouse in Owego

5.0 out of 5 average rating, 14 reviews

Waterfront guesthouse with beautiful view

Oct 20 – 27

€ 160 per night
Guest favorite

Home in Afton

4.93 out of 5 average rating, 15 reviews

Spruce Gardens

Mar 4 – 11

€ 136 per night

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