Cheap Vacations in Anguilla

Choose two or more items and save on your trip:

Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Price was $1,638, price is now $1,483 per person
$1,483
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $6,229, price is now $3,448 per person
$3,448
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Save 100% on your flight
Price was $11,851, price is now $9,942 per person
$9,942
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Save 100% on your flight
Price was $9,328, price is now $7,874 per person
$7,874
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $3,783, price is now $3,263 per person
$3,263
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $2,096, price is now $1,812 per person
$1,812
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was $16,476, price is now $14,857 per person
$14,857
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,899, price is now $1,719 per person
$1,719
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
West End Bay Condos

West End Bay Condos

3 out of 5
Price was $1,721, price is now $1,557 per person
$1,557
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was $3,227, price is now $2,997 per person
$2,997
per person
Dec 18 - Dec 21
found 24 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)

3-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Price was $602, price is now $564 per person
$564
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Ceblue Luxury Villas

Ceblue Luxury Villas

5 out of 5
Price was $2,238, price is now $1,945 per person
$1,945
per person
Dec 18 - Dec 21
found 24 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $1,824, price is now $1,585 per person
$1,585
per person
Dec 18 - Dec 21
found 24 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $3,738, price is now $3,268 per person
$3,268
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was $7,955, price is now $7,306 per person
$7,306
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,312, price is now $1,210 per person
$1,210
per person
Dec 18 - Dec 21
found 24 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was $3,227, price is now $2,997 per person
$2,997
per person
Dec 18 - Dec 21
found 24 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,739, price is now $1,626 per person
$1,626
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Price was $2,924, price is now $2,751 per person
$2,751
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to The Valley (AXA)
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $859, price is now $812 per person
$812
per person
Dec 18 - Dec 21
found 24 hours ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Price was $1,559, price is now $1,486 per person
$1,486
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
West End Bay Condos

West End Bay Condos

3 out of 5
Price was $1,581, price is now $1,514 per person
$1,514
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)

4-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Price was $1,144, price is now $1,094 per person
$1,094
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $4,208, price is now $2,681 per person
$2,681
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Price was $6,443, price is now $5,746 per person
$5,746
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $9,019, price is now $8,061 per person
$8,061
per person
Dec 21 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $2,023, price is now $1,859 per person
$1,859
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Price was $6,831, price is now $6,290 per person
$6,290
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Price was $3,650, price is now $3,377 per person
$3,377
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,654, price is now $1,542 per person
$1,542
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,803, price is now $1,706 per person
$1,706
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
West End Bay Condos

West End Bay Condos

3 out of 5
Price was $1,444, price is now $1,380 per person
$1,380
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Price was $6,809, price is now $6,539 per person
$6,539
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Price was $3,904, price is now $3,753 per person
$3,753
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to The Valley (AXA)

5-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,603, price is now $1,487 per person
$1,487
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $5,127, price is now $3,069 per person
$3,069
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $6,659, price is now $5,213 per person
$5,213
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Save 100% on your flight
Price was $9,056, price is now $7,765 per person
$7,765
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Save 100% on your flight
Price was $7,255, price is now $6,271 per person
$6,271
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $3,227, price is now $2,801 per person
$2,801
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Ceblue Luxury Villas

Ceblue Luxury Villas

5 out of 5
Price was $5,094, price is now $4,448 per person
$4,448
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,928, price is now $1,743 per person
$1,743
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $2,098, price is now $1,898 per person
$1,898
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was $12,290, price is now $11,231 per person
$11,231
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Price was $1,629, price is now $1,508 per person
$1,508
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
West End Bay Condos

West End Bay Condos

3 out of 5
Price was $1,666, price is now $1,555 per person
$1,555
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

6-7 night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Price was $978, price is now $889 per person
$889
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $6,229, price is now $3,448 per person
$3,448
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Save 100% on your flight
Price was $11,851, price is now $9,942 per person
$9,942
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa With Concierge Amenities Pool

6 BR Villa With Concierge Amenities Pool

2 out of 5
Save 100% on your flight
Price was $9,328, price is now $7,874 per person
$7,874
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $3,783, price is now $3,263 per person
$3,263
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $2,096, price is now $1,812 per person
$1,812
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $7,460, price is now $6,708 per person
$6,708
per person
Dec 17 - Dec 24
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was $16,476, price is now $14,857 per person
$14,857
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,899, price is now $1,719 per person
$1,719
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
West End Bay Condos

West End Bay Condos

3 out of 5
Price was $1,721, price is now $1,557 per person
$1,557
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Price was $1,638, price is now $1,483 per person
$1,483
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Ceblue Luxury Villas

Ceblue Luxury Villas

5 out of 5
Price was $6,737, price is now $6,270 per person
$6,270
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

Top places to visit in Anguilla

A beach with clear turquoise waters, white sand, and a palm tree.
FlightsFlightsHotelsHotels

West End Village

West End Village

Flight deals to Anguilla

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 18 - Mon, Dec 21
BOS
Boston
AXA
The Valley
$442 Roundtrip, found 10 hours ago
$442
Roundtrip
found 10 hours ago
Select BermudAir flight, departing Fri, Dec 18 from Boston to The Valley, returning Mon, Dec 21, priced at $442 found 10 hours ago
Sat, Apr 10 - Fri, Apr 16
EWR
New York
AXA
The Valley
$462 Roundtrip, found 1 day ago
$462
Roundtrip
found 1 day ago
Select BermudAir flight, departing Sat, Apr 10 from New York to The Valley, returning Fri, Apr 16, priced at $462 found 1 day ago
Sat, Nov 28 - Sat, Dec 5
ATL
Atlanta
AXA
The Valley
$527 Roundtrip, found 2 days ago
$527
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Nov 28 from Atlanta to The Valley, returning Sat, Dec 5, priced at $527 found 2 days ago

Top rated hotels for your Anguilla vacation

Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

3.5 out of 5
Rendezvous Bay Rendezvous Bay
4.67 mi from city center
$205 nightly
The price is $229 total per night
$229 total
Oct 31 - Nov 1
Total with taxes and fees
With a stay at Anguilla Great House Beach Resort in Rendezvous Bay, you'll be on the beach, within a 10-minute drive of Meads Bay and Rendezvous Bay Beach.
Pool
Spa
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
6.06 mi from city center
$1,023 nightly
The price is $1,139 total per night
$1,139 total
Oct 30 - Oct 31
Total with taxes and fees
When you stay at Four Seasons Resort and Residences Anguilla in West End Village, you'll be on the beach and 10.9 mi (17.6 km) from Shoal Bay Beach.
Pool
Spa
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Free Cancellation
Reserve now, pay when you stay
4.95 mi from city center
$671 nightly
The price is $749 total per night
$749 total
Nov 2 - Nov 3
Total with taxes and fees
When you stay at Aurora Anguilla Resort & Golf Club in Rendezvous Bay, you'll be on the waterfront, you'll be a short 8-minute drive from Blowing Point Ferry Terminal.
Pool
Hot Tub
Don't see what you're looking for?
See all available properties in Anguilla
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.