Hotel Recommendations

Want to make it into an overnight trip?

Make your road trip into a mini-getaway by booking a hotel near your final destination! We've recommended a few overnight options below that suit most price ranges. Clicking the links will reveal the general ending area of your road trip, but it won't ruin all the stops on your trip.

Canadian Trips

Scroll down for the USA

HOTEL RECOMMENDATIONS

Ontario Trips

All the Pretty Things

Luxury suites in a Victorian home in the middle of town

A quaint country inn along the water with live music and great food

A historic B&B with many amenities

An Adventure Is Brewing

A historic adults-only inn with continental breakfast

Use code SG15 to get 15% off your stay at Clonmel Castle!
Your stay includes a Gourmet Made-to-order Breakfast Menu for all guests with Royal Room Service or our famous Dinning-room. On arrival, Guess Where Trips guests will enjoy a Charcuterie Board with Mimosa or Wine! Ensure you note on your reservation that your booking is part of Guess Where Trips.

The ultimate glamping experience with the option for outdoor adventures

Backroad Bliss

This trip ends just southeast of Ottawa, so you can choose any hotel in the Ottawa/Orleans area or easily head home.

Hidden Gems of Huronia

A charming B&B with the tastiest breakfast

A gorgeous historic house in the middle of town

Luxury glamping about 30 minutes from your end destination

A family campground with tent & trailer space + a glamping pod

Hidden Hideaways

A gorgeous French-inspired hotel

Cozy cabins in the woods that are perfect for groups

Hotel rooms within a relaxing resort & spa

Historic Haunts

This hotel is in the center of it all

A funky favourite right outside of town

The most luxurious option around

This trip ends in the greater K/W area, so you can also look at several hotel suggestions here, all of which will be not too far from stops #1 - #4 of this trip.

Hops, Hikes & History

A comfortable hotel right outside of town

The most romantic inn at the center of it all

Local Markets & Picturesque Towns

This hotel is in the center of it all

A funky favourite right outside of town

A gorgeous Inn at the heart of it all

The cutest hotel in a town 30 minutes away

Markets to Mountains

A family-friendly hotel with free breakfast and a pool

A boutique hotel in town with charming rooms and a restaurant on site

A boutique Inn in a converted historic home

Muskoka Meandering

A waterfront resort 20 minutes away with breakfast included

This beautiful lodge near your final stop!

A unique glamping option nearby

Outdoor Adventures & Scenic Roads

An affordable riverside retreat

A relaxing waterfront B & B

Quintessential Quebec

A luxurious hotel which boasts an extraordinary spa and a fine dining restaurant

Comfortable rooms with balconies to enjoy the vast views

A list of unique AirBnB's in the area (prices vary)

Quirky Adventures

A quaint inn in an excellent location with pet-friendly rooms

A historic building turned luxury hotel

A charming old B & B

A riverside inn & cottages with included breakfast

Riverside Roaming

A charming boutique hotel in the centre of town. This is 25 minutes away from the fourth stop

A luxurious getaway option to end your day

A simple hotel offering quite a few amenities

Secrets in the South

A waterfront inn in a beach town 20 minutes away from finishing destination

Check out this cute spot that is near the start of this road trip

Small Town Charm Trail

Southern Express

A funky hotel in the middle of it all

An old farmhouse turned luxury B&B

A cozy loft suite located in the middle of town

Spooky Sights & Ghostly Tales

A classic hotel with a pool and breakfast included

A historic Inn with lots of weekday availability

Taste of the Country

An adorable inn within walking distance to everything

A peaceful B&B outside of town

A waterside Inn 10 minutes from your final stop

The Sweet & Scenic Route

Warm weather cottage and glamping tent rentals

A cozy boutique inn with restaurant on-site

A Bed & Breakfast in a historic home close to your end destination

A great AirBnb for larger groups! Around 30 minutes from your final stop.

Toronto Gems

An all-suite hotel minutes from Toronto's theatre district.

This downtown hotel with breakfast included.

This sophisticated boutique hotel in downtown.

Views & Secret Stops

Waterfront historic Inn from the 1830's

Luxurious and romantic inn

Family-friendly local waterfront hotel

A contemporary hotel with pet-friendly rooms

Vistas & Caves

A resort in the heart of it all

Former mill turned romantic little inn

A unique luxurious glamping experience with pet-friendly rooms

A beautiful hotel room in the centre of a charming town

The Waterfall Route (Purchased before July 30th 2024)

An Instagrammable motel in the center of town

A harbourfront hotel with a pool

A grand victorian Bed & Breakfast

Pet friendly hotel with lots of amenities

The Waterfall Route (Purchased after August 2024)

An adorable B&B in a charming small town ($$)

Countryside year-round glamping cottages ($$)

A luxurious riverside hotel experience ($$$)

Off-grid cabins on an Icelandic sheep farm ($$)

Waterfront Wonders

See a list of available Airbnb options

Check out this cute spot that is near the start of this road trip

Weird & Wonderful Things

A riverside hotel with an interesting and haunted past. Note: this hotel is closer to the first stop

A lovely pet-friendly hotel offering a variety of amenities

An 'Instagrammable' lakeside boutique hotel

A resort with a wide-range of amenities and room types

The Whimsical Route

A cozy private suite with a café on site

A two-night glamping experience with breakfast included and pet-friendly rooms

Wine Time & Hidden Gems

A quaint house offering contemporary suites right in town

Minimalist-chic accommodations in a laid-back lakeside hotel on the beach

An affordable harbourfront inn

Swanky boutique hotel with an upscale restaurant

A historic bed & breakfast with modern luxury

HOTEL RECOMMENDATIONS

Alberta Trips

Peculiar Wonders

A gorgeous hotel with an indoor pool

A great budget friendly option with breakfast included

Quirky Gems

A luxury hotel in the foothills

Riverside cabin rooms with continental breakfast

A cozy B&B in the middle of town

Rocky Mountain Route

This mountain-chic & modern hotel near all the amenities

A chalet-style hotel with pools & mountain views

This valley-view hotel surrounded by nature with the best patio

Rural Adventures

A cozy B&B with great outdoor space and walking distance to downtown

Pet friendly rooms with breakfast included

The Long & Unknown Road

An alpine retreat next to the mountains

Rent a cozy cabin a short drive from the finishing destination

This comfortable resort offers lots of availability and some nice amenities

HOTEL RECOMMENDATIONS

British Columbia Trips

Chasing Waterfalls

Cozy lodge rooms with breathtaking views

A warm pub and hotel known for their pizza

Luxury inn and rustic cabins for a delightful stay

This lakeside lodge with a private beach!

Explore the Shore

This elegant waterfront hotel with a pool

This boutique hotel with panoramic views of the water

This budget-friendly, intimate, harbour-side hotel

Island Gems

A waterfront hotel with a few amenities

Our favourite boutique suites on the island

Secrets on the Scenic Route

This trip has TWO overnight towns for you to choose from:

Option 1: End in Whistler

Option 2: End in Pemberton
All-suite hotel near downtown. Includes free bike or snowshoe rentals

The Taste Trail

A waterfront Inn with free parking

Family friendly hotel with lots of amenities

Boutique hotel with water views

West Coast Wonders

Beautiful glamping cabins near the coast.

Farm stay with ocean and mountain views.

Wilderness resort about 1 hour from your final stop.

HOTEL RECOMMENDATIONS

Nova Scotia Trips

Coastal Crawl

This cozy & historic waterfront inn

A comfortable & well-appointed motel just outside of town

This nautical-themed shoreside motel & cottages

Valley Views

A beach hotel with panorama views of the water

A stately Inn with a garden and a terrace

A modern pet-friendly option in the centre of town

American Trips

Hotel Recommendations

California Trips

Birds, Breezes & Cheeses

Beach cottages & cabins in a charming resort

A hotel on the coast with tons of amenities

A luxury option 30 minutes from your end destination

Coastal Jaunt

Charming updated motel rooms and full cottage rentals

The coolest nautical-style hotel close to the beach

A funky glamping resort with airstreams & tiny cottages

Coffee, Canyons & Coastlines

A boutique hotel right downtown

A standard hotel with a breakfast included

The most charming suites close to local eateries

Colors & Wonders

A hotel with an outdoor pool and pup-friendly rooms

A hotel just 10 minutes from the action

A colorful quirky find right in town that sleeps 12

Country Treasures

A boutique hotel right in town

Cozy rooms at a local inn

Down by the Bay

A quaint English-style inn

A cozy bed and breakfast close to the action

A great pet-friendly option with breakfast included

The Explorer's Route

A standard pet-friendly hotel

This quaint inn that is 15 minutes from your final destination

Forests & Funky Finds

A cozy forest getaway with a hot tub, sleeps up to 6 guests

A historic inn with a Great Gatsby vibe

Luxury glamping options from airstreams to cabins and tents

The coziest hotel among the trees

Joshua Tree Journey

A re-imagined boho motel with the coolest vibe

Luxurious desert glamping with a ton of accommodation styles

An adults-only (and pet-friendly) truly quirky glamping experience

This desert motel was voted one of the best places to stay in Joshua Tree

Ojai Oasis

A gorgeous glamping experience next to a brewery

A mid-century boho beauty with a pool

A boutique B&B in a historic house

A bohemian inn a 15 minute walk to town

Solvang Splendors

A gorgeous historic inn with a gourmet breakfast

Family & pup-friendly glamping close to your end destination

An idyllic renovated motel

Sonoma Sips & Strolls

An elegant Japanese-inspired hotel

A gorgeous hotel with gourmet breakfast and a pool

An updated budget-friendly option with a pool

A hotel & spa in Sonoma

South Bay Secrets

An updated option within walking distance to the beach

A new boutique hotel in the center of town

A fantastic budget-friendly option with an outdoor pool

Tastes & Trails of Malibu

A luxurious beachside hotel with a restaurant

An award-winning complex with cozy bungalows

Topanga Treetops to Beaches

A cozy inn close to your end destination

A renovated historic motel with an outdoor pool

A luxurious beachside hotel with a restaurant

HOTEL RECOMMENDATIONS

Florida Trips

Adventure in the Glades

This beachy-vibes hotel with a pool.

A 1950s motel that is pet-friendly.

Cozy cottages and cabins in a resort with a pool and restaurant

Boardwalks, Brews & Markets

A historic B&B in the middle of town with an amazing breakfast

A "two night minimum stay" inn within walking distance of downtown

Mysteries of Miami

There are tons of hotels near our final stop. Look anywhere around South Miami / Coral Gables / Dadeland / Pinecrest and you will be close to your final destination!

Mysterious Gems

A colorful beachside resort

A luxurious Inn with restaurant on site

Offbeat Oddities

A waterfront B&B surrounded by nature

A comfortable pet-friendly hotel with free breakfast

A sixties-era motel with an updated interior

Old Florida Trail

A modern hotel with an outdoor pool and continental breakfast

A charming B&B with tranquil gardens

A gorgeous and historic Inn

Outback Oasis

This all-suite hotel with a pool and BBQs

Stay in the oldest building in the city, newly renovated in 2023!

A standard hotel with outdoor pool.

Seaside Legends

A hotel full of old-world charm located in the heart of the historic district

Stay in a funky (and pet friendly!) retro motel near the beach

A modern waterfront hotel with an outdoor pool!

A pet-friendly boutique hotel with free breakfast

The Southwest Quest

This cozy waterfront boutique hotel with tons of charm!

This tranquil and upscale hotel in the heart of it all

A comfortable and pet-friendly inn near the beach

A beautiful spa-resort that you'll never want to leave!

Sun-Kissed Surprises

A beachfront hotel that is super close to your final stop

This downtown boutique hotel with tropical decor

A vibrant hotel with a rooftop pool!

Comfortable suites & studios near the beach

Treasure Coast Explorer

A waterside hotel with cozy rooms

A hotel with breakfast included and an outdoor pool

A luxury resort option right in the middle of town

HOTEL RECOMMENDATIONS

Georgia Trips

A Drive Back in Time

A hotel right in the center of town

Riverview rooms in a modern hotel

A cozy hotel option with an outdoor pool

All Things Strange & Beautiful

This quaint southern-style inn in the heart of town

This comfortable & modern hotel with free breakfast and pet-friendly rooms

A modern hotel near the historic downtown with free breakfast & a pool

Film & Food Crawl

A vibrant hotel with a pool and breakfast included

A historic inn just 20 minutes from your end destination

A gorgeous farm escape with modern rooms & peaceful country feels

Mountain Marvels

An AirBnB that is perfect for group getaways! Multiple nights required + sleeps 6

A cozy B&B in the center of town with the best breakfast

A quirky motel just 20 minutes from your last stop

A standard hotel with breakfast included

Quaint Corners

Glamping, cabins and yurts only 20 minutes from your end destination

A stunning resort with an outdoor pool and lots of amenities

Wacky Wonders

A 5-star mountain retreat surrounded by cascading waterfalls.

This boutique hotel in the heart of downtown.

Stay in a cozy and historic lodge-style hotel nestled in the woods.

A unique AirBnB with a "goat experience" and beautiful views.

HOTEL RECOMMENDATIONS

North Carolina

A Little Bit of Everything

We recommend two ending destinations on this trip depending on how far you'd like to drive:

Up to the Mountains:

A nice hotel with an outdoor pool and breakfast included

A chic apartments in the middle of town

Stick Closer to Home:

A hotel with breakfast included and an outdoor pool

An updated hotel with tons of amenities

Antique Adventures

This beautiful inn 20 minutes from your final destination.

A cozy and historic little inn just outside of downtown.

A standard hotel near stop 4 that has a pool.

Picture Perfect Discoveries

This quaint lodge-style hotel in the hills.

Stay in a historic and charming inn.

A beautiful bed & breakfast in a historic home.

Quirky Delights

A historic and cozy Inn in town

A luxurious option for a weekend away

The Road to Asheville

Luxurious but affordable A-frame cabins

An all-suite hotel in an iconic neighborhood

A modern hotel right downtown

Sandhills Sauntering

This historic and romantic tudor-style manor.

A tranquil farm inn that serves breakfast.

Stay in a stunning inn that has a pool and antique bar!

Timeless Towns & Scenic Sips

A historic Inn in a charming small town

A hotel with breakfast included and a swimming pool

A truly NC-inspired boutique hotel about 20 minutes from your end destination

hotel recommendations

DMV (DC, Maryland, Virginia)

Charming Curiosities

A fantastic hotel with breakfast included and an indoor pool

Tons of little cabins on a historic property

A charming inn right in the center of town

Haunts, Hikes & History

A quirky Victorian-style B&B near downtown

A modern hotel with breakfast included

Secrets of Gettysburg

A pet-friendly inn just outside of downtown

A historic 19th century hotel within walking distance of downtown

An updated historic home downtown

Tiny Town Tour

A tranquil and historic inn near your final stop.

This romantic countryside b&b that feels like you're in France!

A pet-friendly bed & breakfast 20 minutes from your final destination.

Waterside Bliss

An updated historic hotel steps from downtown

A standard hotel with free parking, restaurant on-site, and an outdoor pool

3 boutique Inns on the square

Winding Roads & Historic Gems

An Inn right in town with cozy rooms

A resort in a historic building near your end destination

An Inn from 1799 with four cozy rooms to choose from

Hotel Recommendations

North Atlantic & New England

Along the River

Recently renovated historic hotel with a restaurant

A riverside bed and breakfast with a unique view

Riverfront rooms in an Inn with a private patio

An Unusual Adventure

A hotel 15 minutes from your end destination

A great weekday option on a winery

Coastal Connection

An affordable option near your end destination

A historic bed & breakfast near your end destination

A more luxury option on a marina with scenic views

Covered Bridges & Baked Goods

This historic and charming B&B

A luxury option in the middle of town

An ultra-modern & hip hotel with a brewery next door

Enchanted Adventures

A modern hotel that is pet-friendly.

This castle-like hotel with a pool. (also small dog friendly!)

A standard hotel 10 minutes from your final stop.

Escape to the Cape

A historic Inn with a cozy cocktail bar

An adult-only B&B with an outdoor pool

A hotel on a golf course with a private beach

Funky Farms & Storybook Tales

A historic inn in the middle of town

An upscale hotel with an indoor pool

Hudson River Hideaways

An updated hotel with breakfast included

A charming inn on a historic street

A luxury option in the middle of a charming town

Scenic Sights & Tasty Bites

A historic hotel in the middle of town

A comfortable inn with private parking

A hotel just outside of town with an indoor pool

The Shore Explorer

This modern hotel with beachfront and riverfront rooms!

Stay in a romantic and historic riverside inn.

A 21+ social club with elegant hotel rooms above. (adults only)

Vibrant Vistas & Picturesque Towns

A farmstead B&B with cozy rooms

A fantastic affordable option with breakfast included

A hotel with an indoor swimming pool

Vintage Vibes & Views

A gorgeous suite on a historic property / 2 night minimum

A hotel in the middle of town with free breakfast

Whimsical Wonders

This quaint inn that includes daily farmhouse breakfast! (closed in the winter)

A premier farm B&B hidden down a country road

Kids stay free at this countryside hotel! (Max. 2 children under the age of 12)

Witchy Wonders

If you’re traveling during October and want to go inside any of the historical buildings, we recommend having one person in your group read through all four stops and pre-book the attractions you’re interested in.

We especially recommend making this an overnight trip, and doing all of the pre-booked attractions on one day, and your Guess Where Trip the next day.

Click below to see our suggestions:

A renovated midcentury hotel in the center of it all

A historic hotel in the heart of this witchy town

A unique 19th century inn where old world charm meets new world comfort

A gorgeous boutique hotel just 5 minutes from a famous filming location

Hotel Recommendations