Deals on vacations and trips to Rutland

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Rutland flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Trainmasters Inn

Trainmasters Inn

3 out of 5
Price was $468, price is now $443 per person
$443
per person
Jan 23 - Jan 26
found 5 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Worcester (ORH)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning. A library is also provided.

Top Rutland hotels deals

Red Roof Inn Boston - Southborough/ Worcester

Red Roof Inn Boston - Southborough/ Worcester

2 out of 5
367 Turnpike Rd Southborough MA
Free Cancellation
Reserve now, pay when you stay
$65 nightly
The price is $73 total per night
$73 total
Dec 24 - Dec 25
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A picnic area is also provided.
Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

3.5 out of 5
150 Great Wolf Dr Fitchburg MA
$179 nightly
The price is $200 total per night
$200 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This smoke-free resort features free water park access, 4 indoor pools, and a restaurant. Bring the family and enjoy the lazy river, bowling alley, and mini golf. Enjoy the seasonal outdoor pool and unwind at the bar/lounge and poolside bar.
Wellsworth Hotel

Wellsworth Hotel

3 out of 5
14 Mechanic St Southbridge MA
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $108 total per night
$108 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and perks like free self parking.
DoubleTree by Hilton Hotel Boston - Westborough

DoubleTree by Hilton Hotel Boston - Westborough

4 out of 5
5400 Computer Dr Westborough MA
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $109 total per night
$109 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Pool
Parking included
Hilton Garden Inn Worcester

Hilton Garden Inn Worcester

3 out of 5
35 Major Taylor Boulevard Worcester MA
Free Cancellation
Reserve now, pay when you stay
$118 nightly
The price is $135 total per night
$135 total
Dec 25 - Dec 26
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Pool
Hot Tub
Extended Stay America Suites Boston Westborough Computer Dr

Extended Stay America Suites Boston Westborough Computer Dr

2.5 out of 5
1800 Computer Dr Westborough MA
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $90 total per night
$90 total
Dec 27 - Dec 28
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A picnic area and a safe deposit box are also provided.
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Rutland State Park

You can take time to visit Rutland State Park during your travels to Rutland.

Rutland State Park

Frequently asked questions

How much are vacation packages to Rutland?
With a Travelocity vacation package, you could be living it up in Rutland for as low as $443. Hotels, adventures and flights — we have it all. You're bound to save loads just for combining your bookings. And with all that taken care of before you leave, you can sit back, relax and enjoy the adventure.
Where can I get the best vacation package deals for Rutland?
You can score terrific Rutland package deals with Travelocity. Mix and match from 400 airlines and 1,000,000 properties worldwide and turn those vacation daydreams into a reality.
Why should I book my Rutland vacation package via Travelocity?
Nothing beats the peace of mind knowing you've just scored the best deal around — that's our Price Match Guarantee. Add to that our incredibly broad range of magical destinations and 24/7 team of customer service professionals and you've got the blueprint for a stress-free vacation.
Can I save money on my Rutland car rental if I combine it with a hotel or flight?
You sure can — bundle your hotel, flight and car into a Rutland vacation package and you'll save tons. With so much to see and do in and around Rutland, that set of wheels will make exploring a joy. Once you've buckled yourself in, put the stereo on and head toward Fenway Park, a must-see sight approximately 45 mi from Rutland.
Which airport is best for Rutland?
Logan Intl. Airport (BOS) (50 mi away from downtown), Bradley Intl. Airport (BDL) (50 mi away from central Rutland) and T.F. Green Airport (PVD) (50 mi away from central Rutland) are the top options for Rutland.
What is there to do in Rutland?
Rutland State Park deserves a spot on your itinerary. After you've checked off this popular attraction, simply wander the streets of Rutland and experience what makes this vibrant destination tick.
Where should I stay when visiting Rutland?
The VERY LUXURIOUS QUIET AND PEACEFUL APARTMENT ..PRIVATE ENTRANCE is recommended by many travelers. Book soon before it's too late.

Photos of local treasures

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