Pet-friendly holiday rentals in Chesterton
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Top-rated pet-friendly home rentals in Chesterton
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton pet-friendly home rentals
Pet-friendly house rentals
Home in Michigan City
4.85 out of 5 average rating, 105 reviewsThe Blue Herron- Dog friendly
8 – 15 Oct
Home in Manteno
4.95 out of 5 average rating, 172 reviewsManteno Luxury Comfy Cozy home with- 2 king beds!
10 – 17 Nov
Home in South Bend
4.93 out of 5 average rating, 230 reviewsRelax And Enjoy This Cozy Renovated Hidden Gem
7 – 14 Aug
Home in Michigan City
4.9 out of 5 average rating, 339 reviewsBest Deal In Michigan City 1.3 miles to Beach
13 – 20 Aug
Home in Michigan City
4.82 out of 5 average rating, 159 reviewsBeach Getaway House— short walk to the sand!
11 – 18 June
Home in Three Oaks
4.98 out of 5 average rating, 106 reviewsCasa Gitana - Boutique Style Stay in Three Oaks
22 – 29 July
Home in Michigan City
4.85 out of 5 average rating, 110 reviewsLakeshore Manor
28 Dec – 4 Jan
Home in South Bend
4.82 out of 5 average rating, 112 reviewsCharming 3-bedroom home-Freshly remodeled-ND 5 mi.
14 – 21 Oct
Pet-friendly home rentals with a pool
Cottage in Union Pier
4.96 out of 5 average rating, 173 reviewsDesigner Cottage Relax Beach Pool & Spa—Windjammer
13 – 20 Nov
Home in New Buffalo
4.91 out of 5 average rating, 267 reviewsFarmesque with a splash of modern
27 Jan – 3 Feb
Cabin in Union Pier
4.92 out of 5 average rating, 100 reviewsTwo Oaks Cabin - 3 BRs w/ private pool AND hot tub
20 – 27 Dec
Cottage in New Buffalo
4.94 out of 5 average rating, 140 reviewsPerfect Get Away - Private Hot Tub - Lots of Room
31 Mar – 7 Apr
Cottage in New Buffalo
5.0 out of 5 average rating, 137 reviewsCozy New Buffalo Retreat
28 Sept – 5 Oct
Home in Three Oaks
4.9 out of 5 average rating, 103 reviewsLuxe Life | Heated Pool | Hot Tub| Sleeps 10
15 – 22 Oct
Cabin in Benton Harbor
4.91 out of 5 average rating, 290 reviewsCozy Cabin by Nature
26 May – 2 June
Apartment in Chicago
4.87 out of 5 average rating, 110 reviewsLevel ◆ Two Bedroom Deluxe Corner Suite + Balcony
27 Nov – 4 Dec
Private, pet-friendly home rentals
Chalet in La Porte
4.93 out of 5 average rating, 342 reviewsCozy, pet friendly, private home on Pine Lake
23 Feb – 2 Mar
Guesthouse in Sodus Township
4.78 out of 5 average rating, 130 reviewsFarm Cottage
20 – 27 Jan
Loft in Michigan City
4.99 out of 5 average rating, 107 reviewsWanderlust Loft at Lake Michigan
30 Oct – 6 Nov
Guest suite in Three Oaks
4.91 out of 5 average rating, 305 reviewsMaddie’s Place - Deluxe Guest Suite
14 – 21 May
Cabin in Rolling Prairie
4.87 out of 5 average rating, 135 reviews3+ acres of Privacy, Pup heaven!7 minutes 3~Oaks!
2 – 9 Sept
Cottage in Sawyer
4.93 out of 5 average rating, 210 reviewsNorthwind Llama retreat “Chicken coop”
19 – 26 Nov
Apartment in Michigan City
4.87 out of 5 average rating, 141 reviewsPerfect 1 Bed Penthouse Steps To Beach w/Parking!
8 – 15 Dec
Cottage in Union Pier
4.98 out of 5 average rating, 149 reviewsUnion Pier Cottage—Steps to lake, hot tub, sauna!
5 – 12 Sept
Quick stats about holiday rentals that are pet-friendly in Chesterton
Total rentals
20 properties
Wi-Fi availability
20 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.1K reviews
Nightly prices starting at
$61 AUD before taxes and fees
Destinations to explore
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